# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_jus1619
_database_code_depnum_ccdc_archive 'CCDC 2364454'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;University of Alberta
Canada
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(2,6-diiodo-4-methylphenyl)-3-methoxypropan-2-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 I2 O2'
_chemical_formula_sum            'C11 H14 I2 O2'
_chemical_formula_weight         432.02

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   19.9273(8)
_cell_length_b                   8.4314(3)
_cell_length_c                   33.0097(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.2020(5)
_cell_angle_gamma                90
_cell_volume                     5298.0(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9803
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      26.85

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.167
_exptl_crystal_F_000             3232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.113
_exptl_absorpt_coefficient_mu    4.729
_shelx_estimated_absorpt_T_min   0.315
_shelx_estimated_absorpt_T_max   0.617
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3616
_exptl_absorpt_correction_T_max  0.6964
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_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       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48427
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.292
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13041
_reflns_number_gt                11132
_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    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0269P)²+3.2851P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13041
_refine_ls_number_parameters     561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0246
_refine_ls_wR_factor_ref         0.0592
_refine_ls_wR_factor_gt          0.0564
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.004
_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
I1A I 0.13147(2) 0.31000(3) 0.00139(2) 0.03884(5) Uani 1 1 d . . . . .
I2A I 0.02734(2) -0.03393(3) 0.13643(2) 0.03985(6) Uani 1 1 d . . . . .
O1A O 0.23704(11) 0.1923(3) 0.15605(7) 0.0363(5) Uani 1 1 d . . . . .
H1OA H 0.2467(19) 0.242(4) 0.1767(11) 0.043(11) Uiso 1 1 d . . . . .
O2A O 0.18646(11) 0.5179(2) 0.14993(6) 0.0314(4) Uani 1 1 d . . . . .
C1A C 0.14615(14) 0.1240(3) 0.09479(8) 0.0271(6) Uani 1 1 d . . . . .
H1A H 0.1782 0.1329 0.0770 0.033 Uiso 1 1 calc R U . . .
H1B H 0.1516 0.0159 0.1071 0.033 Uiso 1 1 calc R U . . .
C2A C 0.16904(14) 0.2439(3) 0.13101(8) 0.0271(6) Uani 1 1 d . . . . .
H2A H 0.1358 0.2394 0.1485 0.032 Uiso 1 1 calc R U . . .
C3A C 0.17104(14) 0.4105(3) 0.11491(8) 0.0272(6) Uani 1 1 d . . . . .
H3A H 0.2075 0.4189 0.1001 0.033 Uiso 1 1 calc R U . . .
H3B H 0.1251 0.4376 0.0945 0.033 Uiso 1 1 calc R U . . .
C4A C 0.07134(14) 0.1427(3) 0.06648(8) 0.0256(6) Uani 1 1 d . . . . .
C5A C 0.05390(15) 0.2173(3) 0.02672(8) 0.0273(6) Uani 1 1 d . . . . .
C6A C -0.01509(15) 0.2354(4) 0.00138(9) 0.0313(6) Uani 1 1 d . . . . .
H6A H -0.0243 0.2870 -0.0253 0.038 Uiso 1 1 calc R U . . .
C7A C -0.07089(15) 0.1786(3) 0.01469(9) 0.0293(6) Uani 1 1 d . . . . .
C8A C -0.05540(15) 0.1019(3) 0.05326(9) 0.0307(6) Uani 1 1 d . . . . .
H8A H -0.0923 0.0595 0.0627 0.037 Uiso 1 1 calc R U . . .
C9A C 0.01406(15) 0.0861(3) 0.07847(8) 0.0268(6) Uani 1 1 d . . . . .
C10A C -0.14618(16) 0.1969(4) -0.01230(10) 0.0412(8) Uani 1 1 d . . . . .
H10A H -0.1775 0.1524 0.0027 0.049 Uiso 1 1 calc R U . . .
H10B H -0.1531 0.1405 -0.0392 0.049 Uiso 1 1 calc R U . . .
H10C H -0.1568 0.3096 -0.0180 0.049 Uiso 1 1 calc R U . . .
C11A C 0.18541(19) 0.6774(4) 0.13557(11) 0.0443(8) Uani 1 1 d . . . . .
H11A H 0.1961 0.7494 0.1600 0.053 Uiso 1 1 calc R U . . .
H11B H 0.2207 0.6905 0.1205 0.053 Uiso 1 1 calc R U . . .
H11C H 0.1388 0.7021 0.1164 0.053 Uiso 1 1 calc R U . . .
I1B I 0.38848(2) 0.54103(3) 0.38479(2) 0.03626(5) Uani 1 1 d . . . . .
I2B I 0.47347(2) 0.17131(2) 0.24723(2) 0.03291(5) Uani 1 1 d . . . . .
O1B O 0.27477(11) 0.4060(3) 0.22605(6) 0.0296(4) Uani 1 1 d . . . . .
H1OB H 0.2605(19) 0.465(4) 0.2093(11) 0.045(11) Uiso 1 1 d . . . . .
O2B O 0.30744(11) 0.7255(2) 0.22782(6) 0.0333(5) Uani 1 1 d . . . . .
C1B C 0.36352(13) 0.3521(3) 0.29051(8) 0.0250(5) Uani 1 1 d . . . . .
H1C H 0.3334 0.3689 0.3092 0.030 Uiso 1 1 calc R U . . .
H1D H 0.3566 0.2416 0.2800 0.030 Uiso 1 1 calc R U . . .
C2B C 0.34024(14) 0.4657(3) 0.25272(8) 0.0241(5) Uani 1 1 d . . . . .
H2B H 0.3757 0.4638 0.2367 0.029 Uiso 1 1 calc R U . . .
C3B C 0.33112(15) 0.6343(3) 0.26571(8) 0.0274(6) Uani 1 1 d . . . . .
H3C H 0.2962 0.6384 0.2817 0.033 Uiso 1 1 calc R U . . .
H3D H 0.3763 0.6764 0.2840 0.033 Uiso 1 1 calc R U . . .
C4B C 0.43927(13) 0.3740(3) 0.31607(8) 0.0233(5) Uani 1 1 d . . . . .
C5B C 0.46116(14) 0.4548(3) 0.35473(8) 0.0246(5) Uani 1 1 d . . . . .
C6B C 0.53140(15) 0.4811(3) 0.37680(8) 0.0283(6) Uani 1 1 d . . . . .
H6B H 0.5434 0.5394 0.4026 0.034 Uiso 1 1 calc R U . . .
C7B C 0.58379(14) 0.4225(3) 0.36121(8) 0.0259(6) Uani 1 1 d . . . . .
C8B C 0.56485(14) 0.3370(3) 0.32360(8) 0.0265(6) Uani 1 1 d . . . . .
H8B H 0.6000 0.2943 0.3126 0.032 Uiso 1 1 calc R U . . .
C9B C 0.49422(14) 0.3140(3) 0.30203(8) 0.0230(5) Uani 1 1 d . . . . .
C10B C 0.66084(15) 0.4493(4) 0.38475(10) 0.0378(7) Uani 1 1 d . . . . .
H10D H 0.6657 0.5450 0.4022 0.045 Uiso 1 1 calc R U . . .
H10E H 0.6873 0.4623 0.3643 0.045 Uiso 1 1 calc R U . . .
H10F H 0.6791 0.3577 0.4030 0.045 Uiso 1 1 calc R U . . .
C11B C 0.29863(18) 0.8879(4) 0.23608(11) 0.0406(7) Uani 1 1 d . . . . .
H11D H 0.2823 0.9458 0.2092 0.049 Uiso 1 1 calc R U . . .
H11E H 0.2638 0.8983 0.2516 0.049 Uiso 1 1 calc R U . . .
H11F H 0.3436 0.9321 0.2532 0.049 Uiso 1 1 calc R U . . .
I1C I 0.15514(2) 0.26110(2) 0.25370(2) 0.03148(5) Uani 1 1 d . . . . .
I2C I 0.02430(2) -0.04087(2) 0.38174(2) 0.03538(5) Uani 1 1 d . . . . .
O1C O 0.23834(12) 0.1627(3) 0.40966(7) 0.0388(5) Uani 1 1 d . . . . .
H1OC H 0.253(2) 0.217(5) 0.4266(12) 0.057(13) Uiso 1 1 d . . . . .
O2C O 0.19837(12) 0.4836(2) 0.40391(6) 0.0377(5) Uani 1 1 d . . . . .
C1C C 0.15222(13) 0.0965(3) 0.34600(8) 0.0233(5) Uani 1 1 d . . . . .
H1E H 0.1873 0.0989 0.3301 0.028 Uiso 1 1 calc R U . . .
H1F H 0.1534 -0.0106 0.3585 0.028 Uiso 1 1 calc R U . . .
C2C C 0.17309(15) 0.2186(3) 0.38195(8) 0.0293(6) Uani 1 1 d . . . . .
H2C H 0.1371 0.2182 0.3976 0.035 Uiso 1 1 calc R U . . .
C3C C 0.18038(15) 0.3848(3) 0.36710(9) 0.0318(6) Uani 1 1 d . . . . .
H3E H 0.2176 0.3892 0.3528 0.038 Uiso 1 1 calc R U . . .
H3F H 0.1356 0.4204 0.3468 0.038 Uiso 1 1 calc R U . . .
C4C C 0.08040(13) 0.1248(3) 0.31557(8) 0.0221(5) Uani 1 1 d . . . . .
C5C C 0.06954(14) 0.1972(3) 0.27590(8) 0.0246(5) Uani 1 1 d . . . . .
C6C C 0.00338(15) 0.2319(3) 0.24931(9) 0.0299(6) Uani 1 1 d . . . . .
H6C H -0.0013 0.2804 0.2226 0.036 Uiso 1 1 calc R U . . .
C7C C -0.05642(15) 0.1966(3) 0.26112(9) 0.0302(6) Uani 1 1 d . . . . .
C8C C -0.04773(14) 0.1198(3) 0.29948(9) 0.0277(6) Uani 1 1 d . . . . .
H8C H -0.0878 0.0911 0.3079 0.033 Uiso 1 1 calc R U . . .
C9C C 0.01900(14) 0.0845(3) 0.32568(8) 0.0241(5) Uani 1 1 d . . . . .
C10C C -0.12837(16) 0.2390(4) 0.23303(11) 0.0455(8) Uani 1 1 d . . . . .
H10G H -0.1605 0.1502 0.2321 0.055 Uiso 1 1 calc R U . . .
H10H H -0.1261 0.2615 0.2043 0.055 Uiso 1 1 calc R U . . .
H10I H -0.1455 0.3331 0.2444 0.055 Uiso 1 1 calc R U . . .
C11C C 0.19881(19) 0.6458(4) 0.39327(11) 0.0429(8) Uani 1 1 d . . . . .
H11G H 0.2113 0.7097 0.4192 0.052 Uiso 1 1 calc R U . . .
H11H H 0.2333 0.6635 0.3779 0.052 Uiso 1 1 calc R U . . .
H11I H 0.1521 0.6767 0.3753 0.052 Uiso 1 1 calc R U . . .
I1D I 0.37374(2) 0.08056(3) 0.63409(2) 0.03588(5) Uani 1 1 d . . . . .
I2D I 0.47517(2) -0.26087(2) 0.49809(2) 0.03929(6) Uani 1 1 d . . . . .
O1D O 0.26487(12) -0.0389(3) 0.48073(8) 0.0405(5) Uani 1 1 d . . . . .
H1OD H 0.254(2) 0.005(5) 0.4597(12) 0.056(13) Uiso 1 1 d . . . . .
O2D O 0.31751(11) 0.2836(2) 0.48436(6) 0.0337(5) Uani 1 1 d . . . . .
C1D C 0.35821(15) -0.1071(3) 0.54122(9) 0.0290(6) Uani 1 1 d . . . . .
H1G H 0.3268 -0.0981 0.5594 0.035 Uiso 1 1 calc R U . . .
H1H H 0.3534 -0.2160 0.5295 0.035 Uiso 1 1 calc R U . . .
C2D C 0.33379(15) 0.0106(3) 0.50450(9) 0.0281(6) Uani 1 1 d . . . . .
H2D H 0.3656 0.0026 0.4861 0.034 Uiso 1 1 calc R U . . .
C3D C 0.33416(15) 0.1796(3) 0.51993(8) 0.0283(6) Uani 1 1 d . . . . .
H3G H 0.2992 0.1917 0.5357 0.034 Uiso 1 1 calc R U . . .
H3H H 0.3811 0.2061 0.5393 0.034 Uiso 1 1 calc R U . . .
C4D C 0.43310(14) -0.0831(3) 0.56834(8) 0.0263(6) Uani 1 1 d . . . . .
C5D C 0.45118(15) -0.0057(3) 0.60763(9) 0.0282(6) Uani 1 1 d . . . . .
C6D C 0.52017(16) 0.0207(4) 0.63178(9) 0.0323(6) Uani 1 1 d . . . . .
H6D H 0.5297 0.0749 0.6581 0.039 Uiso 1 1 calc R U . . .
C7D C 0.57542(15) -0.0320(3) 0.61752(9) 0.0318(6) Uani 1 1 d . . . . .
C8D C 0.55980(15) -0.1133(3) 0.57940(9) 0.0311(6) Uani 1 1 d . . . . .
H8D H 0.5967 -0.1533 0.5696 0.037 Uiso 1 1 calc R U . . .
C9D C 0.49038(15) -0.1366(3) 0.55545(9) 0.0289(6) Uani 1 1 d . . . . .
C10D C 0.65110(17) -0.0056(4) 0.64304(10) 0.0442(8) Uani 1 1 d . . . . .
H10J H 0.6814 -0.0204 0.6247 0.053 Uiso 1 1 calc R U . . .
H10K H 0.6642 -0.0818 0.6665 0.053 Uiso 1 1 calc R U . . .
H10L H 0.6567 0.1025 0.6544 0.053 Uiso 1 1 calc R U . . .
C11D C 0.31891(19) 0.4447(4) 0.49690(10) 0.0445(8) Uani 1 1 d . . . . .
H11J H 0.3072 0.5127 0.4717 0.053 Uiso 1 1 calc R U . . .
H11K H 0.2845 0.4614 0.5124 0.053 Uiso 1 1 calc R U . . .
H11L H 0.3660 0.4714 0.5152 0.053 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
I1A C5A 2.113(3) . ?
I2A C9A 2.111(3) . ?
O1A C2A 1.430(3) . ?
O2A C11A 1.424(4) . ?
O2A C3A 1.428(3) . ?
C1A C4A 1.515(4) . ?
C1A C2A 1.529(4) . ?
C2A C3A 1.507(4) . ?
C4A C9A 1.398(4) . ?
C4A C5A 1.403(4) . ?
C5A C6A 1.390(4) . ?
C6A C7A 1.396(4) . ?
C7A C8A 1.379(4) . ?
C7A C10A 1.509(4) . ?
C8A C9A 1.395(4) . ?
I1B C5B 2.112(3) . ?
I2B C9B 2.109(3) . ?
O1B C2B 1.432(3) . ?
O2B C11B 1.417(4) . ?
O2B C3B 1.425(3) . ?
C1B C4B 1.507(4) . ?
C1B C2B 1.532(4) . ?
C2B C3B 1.511(4) . ?
C4B C5B 1.397(4) . ?
C4B C9B 1.404(3) . ?
C5B C6B 1.391(4) . ?
C6B C7B 1.385(4) . ?
C7B C8B 1.388(4) . ?
C7B C10B 1.519(4) . ?
C8B C9B 1.390(4) . ?
I1C C5C 2.116(3) . ?
I2C C9C 2.107(3) . ?
O1C C2C 1.430(3) . ?
O2C C11C 1.413(4) . ?
O2C C3C 1.429(3) . ?
C1C C4C 1.505(3) . ?
C1C C2C 1.533(4) . ?
C2C C3C 1.505(4) . ?
C4C C9C 1.402(3) . ?
C4C C5C 1.402(3) . ?
C5C C6C 1.382(4) . ?
C6C C7C 1.391(4) . ?
C7C C8C 1.387(4) . ?
C7C C10C 1.502(4) . ?
C8C C9C 1.387(4) . ?
I1D C5D 2.114(3) . ?
I2D C9D 2.106(3) . ?
O1D C2D 1.428(4) . ?
O2D C11D 1.418(4) . ?
O2D C3D 1.424(3) . ?
C1D C4D 1.510(4) . ?
C1D C2D 1.531(4) . ?
C2D C3D 1.513(4) . ?
C4D C5D 1.401(4) . ?
C4D C9D 1.405(4) . ?
C5D C6D 1.388(4) . ?
C6D C7D 1.392(4) . ?
C7D C8D 1.385(4) . ?
C7D C10D 1.511(4) . ?
C8D C9D 1.389(4) . ?

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
C11A O2A C3A 110.5(2) . . ?
C4A C1A C2A 115.2(2) . . ?
O1A C2A C3A 111.6(2) . . ?
O1A C2A C1A 105.3(2) . . ?
C3A C2A C1A 112.0(2) . . ?
O2A C3A C2A 109.1(2) . . ?
C9A C4A C5A 114.9(2) . . ?
C9A C4A C1A 121.8(2) . . ?
C5A C4A C1A 123.3(2) . . ?
C6A C5A C4A 122.6(3) . . ?
C6A C5A I1A 115.5(2) . . ?
C4A C5A I1A 121.9(2) . . ?
C5A C6A C7A 120.7(3) . . ?
C8A C7A C6A 118.0(3) . . ?
C8A C7A C10A 120.3(3) . . ?
C6A C7A C10A 121.6(3) . . ?
C7A C8A C9A 120.5(3) . . ?
C8A C9A C4A 123.2(3) . . ?
C8A C9A I2A 115.0(2) . . ?
C4A C9A I2A 121.7(2) . . ?
C11B O2B C3B 112.4(2) . . ?
C4B C1B C2B 113.0(2) . . ?
O1B C2B C3B 109.9(2) . . ?
O1B C2B C1B 106.4(2) . . ?
C3B C2B C1B 112.9(2) . . ?
O2B C3B C2B 107.2(2) . . ?
C5B C4B C9B 114.4(2) . . ?
C5B C4B C1B 124.2(2) . . ?
C9B C4B C1B 121.4(2) . . ?
C6B C5B C4B 123.4(2) . . ?
C6B C5B I1B 114.98(19) . . ?
C4B C5B I1B 121.63(19) . . ?
C7B C6B C5B 120.0(3) . . ?
C6B C7B C8B 118.8(2) . . ?
C6B C7B C10B 121.1(3) . . ?
C8B C7B C10B 120.1(2) . . ?
C7B C8B C9B 119.8(2) . . ?
C8B C9B C4B 123.4(2) . . ?
C8B C9B I2B 115.52(19) . . ?
C4B C9B I2B 120.98(19) . . ?
C11C O2C C3C 111.8(2) . . ?
C4C C1C C2C 113.4(2) . . ?
O1C C2C C3C 111.0(2) . . ?
O1C C2C C1C 105.1(2) . . ?
C3C C2C C1C 113.8(2) . . ?
O2C C3C C2C 106.9(2) . . ?
C9C C4C C5C 115.0(2) . . ?
C9C C4C C1C 121.8(2) . . ?
C5C C4C C1C 123.1(2) . . ?
C6C C5C C4C 122.7(2) . . ?
C6C C5C I1C 116.2(2) . . ?
C4C C5C I1C 121.11(19) . . ?
C5C C6C C7C 120.8(3) . . ?
C8C C7C C6C 118.0(3) . . ?
C8C C7C C10C 120.9(3) . . ?
C6C C7C C10C 121.1(3) . . ?
C9C C8C C7C 120.5(3) . . ?
C8C C9C C4C 122.9(2) . . ?
C8C C9C I2C 116.41(19) . . ?
C4C C9C I2C 120.68(19) . . ?
C11D O2D C3D 111.7(2) . . ?
C4D C1D C2D 114.2(2) . . ?
O1D C2D C3D 111.6(2) . . ?
O1D C2D C1D 105.9(2) . . ?
C3D C2D C1D 112.0(2) . . ?
O2D C3D C2D 109.0(2) . . ?
C5D C4D C9D 114.9(3) . . ?
C5D C4D C1D 123.4(2) . . ?
C9D C4D C1D 121.8(3) . . ?
C6D C5D C4D 123.1(3) . . ?
C6D C5D I1D 115.3(2) . . ?
C4D C5D I1D 121.6(2) . . ?
C5D C6D C7D 120.2(3) . . ?
C8D C7D C6D 118.5(3) . . ?
C8D C7D C10D 119.9(3) . . ?
C6D C7D C10D 121.6(3) . . ?
C7D C8D C9D 120.4(3) . . ?
C8D C9D C4D 122.9(3) . . ?
C8D C9D I2D 115.9(2) . . ?
C4D C9D I2D 121.2(2) . . ?

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
C4A C1A C2A O1A 173.2(2) . . . . ?
C4A C1A C2A C3A -65.4(3) . . . . ?
C11A O2A C3A C2A -177.2(2) . . . . ?
O1A C2A C3A O2A -67.5(3) . . . . ?
C1A C2A C3A O2A 174.8(2) . . . . ?
C2A C1A C4A C9A -79.5(3) . . . . ?
C2A C1A C4A C5A 100.3(3) . . . . ?
C9A C4A C5A C6A 0.8(4) . . . . ?
C1A C4A C5A C6A -179.1(3) . . . . ?
C9A C4A C5A I1A -179.25(19) . . . . ?
C1A C4A C5A I1A 0.9(4) . . . . ?
C4A C5A C6A C7A -0.2(4) . . . . ?
I1A C5A C6A C7A 179.9(2) . . . . ?
C5A C6A C7A C8A -1.1(4) . . . . ?
C5A C6A C7A C10A -180.0(3) . . . . ?
C6A C7A C8A C9A 1.7(4) . . . . ?
C10A C7A C8A C9A -179.4(3) . . . . ?
C7A C8A C9A C4A -1.1(4) . . . . ?
C7A C8A C9A I2A 179.8(2) . . . . ?
C5A C4A C9A C8A -0.1(4) . . . . ?
C1A C4A C9A C8A 179.7(3) . . . . ?
C5A C4A C9A I2A 178.92(19) . . . . ?
C1A C4A C9A I2A -1.2(4) . . . . ?
C4B C1B C2B O1B 165.9(2) . . . . ?
C4B C1B C2B C3B -73.4(3) . . . . ?
C11B O2B C3B C2B -178.5(2) . . . . ?
O1B C2B C3B O2B -59.5(3) . . . . ?
C1B C2B C3B O2B -178.2(2) . . . . ?
C2B C1B C4B C5B 101.9(3) . . . . ?
C2B C1B C4B C9B -77.6(3) . . . . ?
C9B C4B C5B C6B 3.0(4) . . . . ?
C1B C4B C5B C6B -176.5(3) . . . . ?
C9B C4B C5B I1B -175.32(18) . . . . ?
C1B C4B C5B I1B 5.2(4) . . . . ?
C4B C5B C6B C7B -1.8(4) . . . . ?
I1B C5B C6B C7B 176.6(2) . . . . ?
C5B C6B C7B C8B -0.3(4) . . . . ?
C5B C6B C7B C10B -179.8(3) . . . . ?
C6B C7B C8B C9B 1.0(4) . . . . ?
C10B C7B C8B C9B -179.5(3) . . . . ?
C7B C8B C9B C4B 0.4(4) . . . . ?
C7B C8B C9B I2B -176.8(2) . . . . ?
C5B C4B C9B C8B -2.3(4) . . . . ?
C1B C4B C9B C8B 177.2(2) . . . . ?
C5B C4B C9B I2B 174.68(18) . . . . ?
C1B C4B C9B I2B -5.8(3) . . . . ?
C4C C1C C2C O1C 173.8(2) . . . . ?
C4C C1C C2C C3C -64.6(3) . . . . ?
C11C O2C C3C C2C -173.3(2) . . . . ?
O1C C2C C3C O2C -62.9(3) . . . . ?
C1C C2C C3C O2C 178.8(2) . . . . ?
C2C C1C C4C C9C -77.0(3) . . . . ?
C2C C1C C4C C5C 100.9(3) . . . . ?
C9C C4C C5C C6C 2.3(4) . . . . ?
C1C C4C C5C C6C -175.8(3) . . . . ?
C9C C4C C5C I1C -178.12(18) . . . . ?
C1C C4C C5C I1C 3.8(4) . . . . ?
C4C C5C C6C C7C 0.4(4) . . . . ?
I1C C5C C6C C7C -179.2(2) . . . . ?
C5C C6C C7C C8C -2.7(4) . . . . ?
C5C C6C C7C C10C 177.9(3) . . . . ?
C6C C7C C8C C9C 2.1(4) . . . . ?
C10C C7C C8C C9C -178.4(3) . . . . ?
C7C C8C C9C C4C 0.7(4) . . . . ?
C7C C8C C9C I2C -177.5(2) . . . . ?
C5C C4C C9C C8C -2.9(4) . . . . ?
C1C C4C C9C C8C 175.2(2) . . . . ?
C5C C4C C9C I2C 175.30(18) . . . . ?
C1C C4C C9C I2C -6.6(3) . . . . ?
C4D C1D C2D O1D 175.2(2) . . . . ?
C4D C1D C2D C3D -62.9(3) . . . . ?
C11D O2D C3D C2D -178.4(2) . . . . ?
O1D C2D C3D O2D -66.9(3) . . . . ?
C1D C2D C3D O2D 174.5(2) . . . . ?
C2D C1D C4D C5D 100.6(3) . . . . ?
C2D C1D C4D C9D -78.8(3) . . . . ?
C9D C4D C5D C6D 1.6(4) . . . . ?
C1D C4D C5D C6D -177.8(3) . . . . ?
C9D C4D C5D I1D -178.67(19) . . . . ?
C1D C4D C5D I1D 1.9(4) . . . . ?
C4D C5D C6D C7D -0.7(4) . . . . ?
I1D C5D C6D C7D 179.6(2) . . . . ?
C5D C6D C7D C8D -1.2(4) . . . . ?
C5D C6D C7D C10D -179.9(3) . . . . ?
C6D C7D C8D C9D 2.1(4) . . . . ?
C10D C7D C8D C9D -179.3(3) . . . . ?
C7D C8D C9D C4D -1.1(4) . . . . ?
C7D C8D C9D I2D 179.6(2) . . . . ?
C5D C4D C9D C8D -0.8(4) . . . . ?
C1D C4D C9D C8D 178.7(3) . . . . ?
C5D C4D C9D I2D 178.53(19) . . . . ?
C1D C4D C9D I2D -2.0(4) . . . . ?

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
O1A H1OA O1B 0.78(3) 2.08(4) 2.850(3) 171(4) .
O1B H1OB O2A 0.74(4) 2.12(4) 2.772(3) 147(4) .
O1C H1OC O2D 0.71(4) 2.04(4) 2.703(3) 155(4) .
O1D H1OD O1C 0.76(4) 2.07(4) 2.818(3) 168(4) .

_refine_diff_density_max         0.798
_refine_diff_density_min         -1.050
_refine_diff_density_rms         0.128


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and dichloromethane'
####################################################################### 
# 
# 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_jus1617
_database_code_depnum_ccdc_archive 'CCDC 2364455'
loop_
_audit_author_name
_audit_author_address
'Robert McDonald'
;University of Alberta
Canada
;
_audit_update_record             
;
2024-06-21 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-(2,6-diiodo-4-methylphenyl)-3-(2-methoxyphenoxy)propan-2-ol
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H18 I2 O3'
_chemical_formula_sum            'C17 H18 I2 O3'
_chemical_formula_weight         524.11

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.6792(4)
_cell_length_b                   29.0562(9)
_cell_length_c                   5.62368(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.355(2)
_cell_angle_gamma                90
_cell_volume                     1743.54(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      74.00

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    28.414
_shelx_estimated_absorpt_T_min   0.041
_shelx_estimated_absorpt_T_max   0.396
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.4831
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            11975
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.042
_diffrn_reflns_theta_max         74.089
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3517
_reflns_number_gt                3075
_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    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0501P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3517
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0834
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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_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 0.13498(3) 0.08465(2) -0.52957(5) 0.03591(10) Uani 1 1 d . . . . .
I2 I -0.16250(2) 0.19914(2) 0.17704(5) 0.03350(9) Uani 1 1 d . . . . .
O1 O 0.2094(3) 0.23473(10) -0.1249(6) 0.0352(7) Uani 1 1 d . . . . .
H1O H 0.233(5) 0.2464(19) -0.017(10) 0.031(14) Uiso 1 1 d . . . . .
O2 O 0.3423(3) 0.16776(10) 0.1542(5) 0.0314(6) Uani 1 1 d . . . . .
O3 O 0.4729(3) 0.19215(12) 0.5218(6) 0.0426(8) Uani 1 1 d . . . . .
C1 C 0.0513(4) 0.18029(13) -0.2347(7) 0.0256(7) Uani 1 1 d . . . . .
H1A H -0.0068 0.2068 -0.2498 0.031 Uiso 1 1 calc R U . . .
H1B H 0.0881 0.1754 -0.3916 0.031 Uiso 1 1 calc R U . . .
C2 C 0.1567(4) 0.19207(13) -0.0512(7) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.1208 0.1959 0.1090 0.030 Uiso 1 1 calc R U . . .
C3 C 0.2574(4) 0.15537(13) -0.0384(7) 0.0252(7) Uani 1 1 d . . . . .
H3A H 0.2200 0.1248 -0.0094 0.030 Uiso 1 1 calc R U . . .
H3B H 0.3018 0.1541 -0.1894 0.030 Uiso 1 1 calc R U . . .
C4 C -0.0224(4) 0.13768(13) -0.1705(7) 0.0253(7) Uani 1 1 d . . . . .
C5 C -0.0023(4) 0.09441(14) -0.2745(7) 0.0273(8) Uani 1 1 d . . . . .
C6 C -0.0661(4) 0.05514(14) -0.2126(8) 0.0309(8) Uani 1 1 d . . . . .
H6 H -0.0489 0.0268 -0.2894 0.037 Uiso 1 1 calc R U . . .
C7 C -0.1554(4) 0.05655(15) -0.0388(8) 0.0305(8) Uani 1 1 d . . . . .
C8 C -0.1801(4) 0.09896(15) 0.0646(8) 0.0305(8) Uani 1 1 d . . . . .
H8 H -0.2413 0.1013 0.1820 0.037 Uiso 1 1 calc R U . . .
C9 C -0.1152(4) 0.13797(12) -0.0039(7) 0.0253(7) Uani 1 1 d . . . . .
C10 C -0.2220(4) 0.01336(16) 0.0364(10) 0.0431(11) Uani 1 1 d . . . . .
H10A H -0.3082 0.0136 -0.0304 0.052 Uiso 1 1 calc R U . . .
H10B H -0.2231 0.0122 0.2104 0.052 Uiso 1 1 calc R U . . .
H10C H -0.1779 -0.0137 -0.0221 0.052 Uiso 1 1 calc R U . . .
C11 C 0.4170(4) 0.13413(14) 0.2523(8) 0.0287(8) Uani 1 1 d . . . . .
C12 C 0.4873(4) 0.14749(16) 0.4560(8) 0.0330(9) Uani 1 1 d . . . . .
C13 C 0.5633(4) 0.1153(2) 0.5766(9) 0.0446(12) Uani 1 1 d . . . . .
H13 H 0.6121 0.1242 0.7140 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5672(5) 0.0705(2) 0.4951(11) 0.0507(14) Uani 1 1 d . . . . .
H14 H 0.6177 0.0485 0.5795 0.061 Uiso 1 1 calc R U . . .
C15 C 0.4989(4) 0.05721(17) 0.2931(10) 0.0412(11) Uani 1 1 d . . . . .
H15 H 0.5026 0.0263 0.2394 0.049 Uiso 1 1 calc R U . . .
C16 C 0.4242(4) 0.08934(15) 0.1669(8) 0.0321(9) Uani 1 1 d . . . . .
H16 H 0.3790 0.0806 0.0250 0.039 Uiso 1 1 calc R U . . .
C17 C 0.5473(6) 0.2087(2) 0.7215(9) 0.0554(15) Uani 1 1 d . . . . .
H17A H 0.5277 0.2411 0.7494 0.067 Uiso 1 1 calc R U . . .
H17B H 0.5287 0.1906 0.8630 0.067 Uiso 1 1 calc R U . . .
H17C H 0.6363 0.2055 0.6889 0.067 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 C5 2.112(4) . ?
I2 C9 2.119(4) . ?
O1 C2 1.430(5) . ?
O2 C11 1.364(5) . ?
O2 C3 1.429(4) . ?
O3 C12 1.360(6) . ?
O3 C17 1.432(6) . ?
C1 C4 1.519(5) . ?
C1 C2 1.534(5) . ?
C2 C3 1.515(5) . ?
C4 C9 1.391(6) . ?
C4 C5 1.407(5) . ?
C5 C6 1.381(6) . ?
C6 C7 1.394(6) . ?
C7 C8 1.392(6) . ?
C7 C10 1.511(6) . ?
C8 C9 1.391(5) . ?
C11 C16 1.391(6) . ?
C11 C12 1.398(6) . ?
C12 C13 1.395(6) . ?
C13 C14 1.382(8) . ?
C14 C15 1.380(8) . ?
C15 C16 1.402(6) . ?

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
C11 O2 C3 117.9(3) . . ?
C12 O3 C17 117.9(4) . . ?
C4 C1 C2 113.3(3) . . ?
O1 C2 C3 109.7(3) . . ?
O1 C2 C1 106.6(3) . . ?
C3 C2 C1 112.0(3) . . ?
O2 C3 C2 106.6(3) . . ?
C9 C4 C5 114.2(4) . . ?
C9 C4 C1 123.1(3) . . ?
C5 C4 C1 122.7(4) . . ?
C6 C5 C4 123.3(4) . . ?
C6 C5 I1 115.1(3) . . ?
C4 C5 I1 121.6(3) . . ?
C5 C6 C7 120.7(4) . . ?
C8 C7 C6 117.7(4) . . ?
C8 C7 C10 121.3(4) . . ?
C6 C7 C10 121.0(4) . . ?
C9 C8 C7 120.0(4) . . ?
C4 C9 C8 123.9(4) . . ?
C4 C9 I2 121.3(3) . . ?
C8 C9 I2 114.8(3) . . ?
O2 C11 C16 124.8(4) . . ?
O2 C11 C12 114.7(4) . . ?
C16 C11 C12 120.5(4) . . ?
O3 C12 C13 125.2(4) . . ?
O3 C12 C11 115.2(4) . . ?
C13 C12 C11 119.6(5) . . ?
C14 C13 C12 119.7(5) . . ?
C15 C14 C13 121.0(5) . . ?
C14 C15 C16 120.1(5) . . ?
C11 C16 C15 119.1(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
C4 C1 C2 O1 -175.0(3) . . . . ?
C4 C1 C2 C3 65.1(4) . . . . ?
C11 O2 C3 C2 159.5(3) . . . . ?
O1 C2 C3 O2 67.9(4) . . . . ?
C1 C2 C3 O2 -174.0(3) . . . . ?
C2 C1 C4 C9 79.0(5) . . . . ?
C2 C1 C4 C5 -100.8(4) . . . . ?
C9 C4 C5 C6 -1.8(6) . . . . ?
C1 C4 C5 C6 178.0(4) . . . . ?
C9 C4 C5 I1 -179.2(3) . . . . ?
C1 C4 C5 I1 0.6(5) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
I1 C5 C6 C7 177.3(3) . . . . ?
C5 C6 C7 C8 1.7(6) . . . . ?
C5 C6 C7 C10 -177.6(4) . . . . ?
C6 C7 C8 C9 -0.9(6) . . . . ?
C10 C7 C8 C9 178.4(4) . . . . ?
C5 C4 C9 C8 2.6(6) . . . . ?
C1 C4 C9 C8 -177.2(4) . . . . ?
C5 C4 C9 I2 180.0(3) . . . . ?
C1 C4 C9 I2 0.1(5) . . . . ?
C7 C8 C9 C4 -1.4(7) . . . . ?
C7 C8 C9 I2 -178.9(3) . . . . ?
C3 O2 C11 C16 5.4(6) . . . . ?
C3 O2 C11 C12 -173.2(3) . . . . ?
C17 O3 C12 C13 4.3(7) . . . . ?
C17 O3 C12 C11 -176.7(4) . . . . ?
O2 C11 C12 O3 -1.6(5) . . . . ?
C16 C11 C12 O3 179.8(4) . . . . ?
O2 C11 C12 C13 177.5(4) . . . . ?
C16 C11 C12 C13 -1.2(6) . . . . ?
O3 C12 C13 C14 178.2(5) . . . . ?
C11 C12 C13 C14 -0.8(7) . . . . ?
C12 C13 C14 C15 1.3(8) . . . . ?
C13 C14 C15 C16 0.1(7) . . . . ?
O2 C11 C16 C15 -176.0(4) . . . . ?
C12 C11 C16 C15 2.5(6) . . . . ?
C14 C15 C16 C11 -2.0(7) . . . . ?

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
O1 H1O O1 0.73(6) 2.29(6) 2.9485(18) 150(6) 4_566

_refine_diff_density_max         1.066
_refine_diff_density_min         -1.399
_refine_diff_density_rms         0.129


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexanes and dichloromethane'
