# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_bo3130
_database_code_depnum_ccdc_archive 'CCDC 1027228'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C4OB02551B 2015
_audit_update_record             
;
2014-10-01 deposited with the CCDC.
2015-01-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          407
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 I O5'
_chemical_formula_weight         454.24

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.304(5)
_cell_length_b                   4.5035(12)
_cell_length_c                   21.714(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.318(3)
_cell_angle_gamma                90.00
_cell_volume                     1782.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    163(2)
_cell_measurement_reflns_used    6658
_cell_measurement_theta_min      2.235
_cell_measurement_theta_max      31.497

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.3883
_exptl_absorpt_correction_T_max  0.7409
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      163(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19004
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         31.00
_reflns_number_total             5623
_reflns_number_gt                4744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.2260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5623
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1261
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.009005(9) -0.00361(4) 0.342451(8) 0.02979(9) Uani 1 1 d . . .
O1 O 0.28780(9) 0.6564(4) 0.27271(8) 0.0238(3) Uani 1 1 d . . .
O2 O 0.40652(10) 0.3542(5) 0.37560(8) 0.0337(4) Uani 1 1 d . . .
O3 O 0.47226(11) 0.6284(5) 0.31523(9) 0.0415(5) Uani 1 1 d . . .
O4 O 0.17268(12) -0.0112(4) 0.02516(9) 0.0281(4) Uani 1 1 d . . .
O5 O 0.30393(9) 0.2202(4) 0.01172(7) 0.0260(3) Uani 1 1 d . . .
C1 C 0.10711(12) 0.1940(5) 0.32052(10) 0.0223(4) Uani 1 1 d . . .
C2 C 0.14299(14) 0.3911(6) 0.36191(11) 0.0268(5) Uani 1 1 d . . .
H2 H 0.1251 0.4264 0.4010 0.032 Uiso 1 1 calc R . .
C3 C 0.20497(16) 0.5358(5) 0.34585(12) 0.0256(5) Uani 1 1 d . . .
H3 H 0.2305 0.6690 0.3741 0.031 Uiso 1 1 calc R . .
C4 C 0.23002(15) 0.4859(4) 0.28799(12) 0.0212(5) Uani 1 1 d . . .
C5 C 0.19470(11) 0.2843(5) 0.24578(9) 0.0199(4) Uani 1 1 d . . .
C6 C 0.13295(12) 0.1372(5) 0.26353(10) 0.0214(4) Uani 1 1 d . . .
H6 H 0.1083 -0.0034 0.2364 0.026 Uiso 1 1 calc R . .
C7 C 0.22258(12) 0.2571(5) 0.18448(9) 0.0202(4) Uani 1 1 d . . .
C8 C 0.18158(13) 0.1199(5) 0.13473(10) 0.0218(4) Uani 1 1 d . . .
H8 H 0.1354 0.0329 0.1404 0.026 Uiso 1 1 calc R . .
C9 C 0.20854(13) 0.1114(5) 0.07700(10) 0.0224(4) Uani 1 1 d . . .
C10 C 0.27684(12) 0.2416(5) 0.06887(10) 0.0230(4) Uani 1 1 d . . .
C11 C 0.31789(12) 0.3811(5) 0.11763(10) 0.0220(4) Uani 1 1 d . . .
C12 C 0.29052(12) 0.3827(5) 0.17590(10) 0.0208(4) Uani 1 1 d . . .
C13 C 0.33443(15) 0.5173(4) 0.23135(12) 0.0208(5) Uani 1 1 d . . .
H13 H 0.3668 0.6743 0.2160 0.025 Uiso 1 1 calc R . .
C14 C 0.38376(12) 0.2888(5) 0.26743(10) 0.0214(4) Uani 1 1 d . . .
H14A H 0.3533 0.1290 0.2832 0.026 Uiso 1 1 calc R . .
H14B H 0.4177 0.1982 0.2399 0.026 Uiso 1 1 calc R . .
C15 C 0.42685(14) 0.4422(6) 0.32067(12) 0.0240(5) Uani 1 1 d . . .
C16 C 0.4426(2) 0.5065(7) 0.42848(15) 0.0412(8) Uani 1 1 d . . .
H16A H 0.4948 0.4541 0.4329 0.049 Uiso 1 1 calc R . .
H16B H 0.4202 0.4473 0.4659 0.049 Uiso 1 1 calc R . .
H16C H 0.4374 0.7214 0.4226 0.049 Uiso 1 1 calc R . .
C17 C 0.39019(16) 0.5279(5) 0.10699(14) 0.0278(5) Uani 1 1 d . . .
H17A H 0.4009 0.4948 0.0641 0.033 Uiso 1 1 calc R . .
H17B H 0.4295 0.4421 0.1352 0.033 Uiso 1 1 calc R . .
H17C H 0.3869 0.7416 0.1147 0.033 Uiso 1 1 calc R . .
C18 C 0.10704(14) -0.1717(7) 0.03321(12) 0.0333(6) Uani 1 1 d . . .
H18A H 0.1175 -0.3263 0.0646 0.040 Uiso 1 1 calc R . .
H18B H 0.0886 -0.2638 -0.0061 0.040 Uiso 1 1 calc R . .
H18C H 0.0700 -0.0353 0.0467 0.040 Uiso 1 1 calc R . .
C19 C 0.27845(18) 0.4514(6) -0.03034(13) 0.0288(5) Uani 1 1 d . . .
H19A H 0.2249 0.4400 -0.0382 0.035 Uiso 1 1 calc R . .
H19B H 0.3007 0.4273 -0.0694 0.035 Uiso 1 1 calc R . .
H19C H 0.2923 0.6450 -0.0122 0.035 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 C1 2.098(2) . ?
O1 C4 1.372(3) . ?
O1 C13 1.439(3) . ?
O2 C15 1.342(3) . ?
O2 C16 1.444(3) . ?
O3 C15 1.194(3) . ?
O4 C9 1.366(3) . ?
O4 C18 1.427(3) . ?
O5 C10 1.382(3) . ?
O5 C19 1.434(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.389(3) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.395(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(3) . ?
C5 C6 1.395(3) . ?
C5 C7 1.474(3) . ?
C6 H6 0.9500 . ?
C7 C12 1.394(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(3) . ?
C10 C11 1.390(3) . ?
C11 C12 1.403(3) . ?
C11 C17 1.516(4) . ?
C12 C13 1.511(3) . ?
C13 C14 1.535(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.505(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C4 O1 C13 114.97(17) . . ?
C15 O2 C16 115.0(2) . . ?
C9 O4 C18 116.7(2) . . ?
C10 O5 C19 113.50(19) . . ?
C2 C1 C6 121.1(2) . . ?
C2 C1 I1 119.27(17) . . ?
C6 C1 I1 119.56(16) . . ?
C3 C2 C1 119.3(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O1 C4 C3 116.9(2) . . ?
O1 C4 C5 121.5(2) . . ?
C3 C4 C5 121.5(2) . . ?
C6 C5 C4 117.6(2) . . ?
C6 C5 C7 124.54(19) . . ?
C4 C5 C7 117.8(2) . . ?
C1 C6 C5 120.7(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C12 C7 C8 119.8(2) . . ?
C12 C7 C5 118.34(19) . . ?
C8 C7 C5 121.8(2) . . ?
C9 C8 C7 119.9(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
O4 C9 C8 124.8(2) . . ?
O4 C9 C10 115.5(2) . . ?
C8 C9 C10 119.7(2) . . ?
O5 C10 C11 120.1(2) . . ?
O5 C10 C9 118.7(2) . . ?
C11 C10 C9 121.1(2) . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 C17 119.9(2) . . ?
C12 C11 C17 121.7(2) . . ?
C7 C12 C11 121.1(2) . . ?
C7 C12 C13 118.1(2) . . ?
C11 C12 C13 120.8(2) . . ?
O1 C13 C12 111.7(2) . . ?
O1 C13 C14 109.2(2) . . ?
C12 C13 C14 112.45(17) . . ?
O1 C13 H13 107.8 . . ?
C12 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C15 C14 C13 109.02(19) . . ?
C15 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
O3 C15 O2 123.2(2) . . ?
O3 C15 C14 124.5(2) . . ?
O2 C15 C14 112.2(2) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
C6 C1 C2 C3 0.8(4) . . . . ?
I1 C1 C2 C3 -175.87(19) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C13 O1 C4 C3 150.7(2) . . . . ?
C13 O1 C4 C5 -33.4(3) . . . . ?
C2 C3 C4 O1 174.2(2) . . . . ?
C2 C3 C4 C5 -1.7(4) . . . . ?
O1 C4 C5 C6 -175.1(2) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
O1 C4 C5 C7 1.1(3) . . . . ?
C3 C4 C5 C7 176.9(2) . . . . ?
C2 C1 C6 C5 -1.9(3) . . . . ?
I1 C1 C6 C5 174.73(16) . . . . ?
C4 C5 C6 C1 1.2(3) . . . . ?
C7 C5 C6 C1 -174.8(2) . . . . ?
C6 C5 C7 C12 -171.0(2) . . . . ?
C4 C5 C7 C12 13.1(3) . . . . ?
C6 C5 C7 C8 11.5(3) . . . . ?
C4 C5 C7 C8 -164.4(2) . . . . ?
C12 C7 C8 C9 -0.4(3) . . . . ?
C5 C7 C8 C9 177.0(2) . . . . ?
C18 O4 C9 C8 -7.8(4) . . . . ?
C18 O4 C9 C10 173.7(2) . . . . ?
C7 C8 C9 O4 -178.7(2) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C19 O5 C10 C11 -95.6(3) . . . . ?
C19 O5 C10 C9 86.5(3) . . . . ?
O4 C9 C10 O5 -3.9(3) . . . . ?
C8 C9 C10 O5 177.5(2) . . . . ?
O4 C9 C10 C11 178.2(2) . . . . ?
C8 C9 C10 C11 -0.4(4) . . . . ?
O5 C10 C11 C12 -176.2(2) . . . . ?
C9 C10 C11 C12 1.7(3) . . . . ?
O5 C10 C11 C17 4.0(3) . . . . ?
C9 C10 C11 C17 -178.1(2) . . . . ?
C8 C7 C12 C11 1.7(3) . . . . ?
C5 C7 C12 C11 -175.8(2) . . . . ?
C8 C7 C12 C13 -177.5(2) . . . . ?
C5 C7 C12 C13 4.9(3) . . . . ?
C10 C11 C12 C7 -2.3(3) . . . . ?
C17 C11 C12 C7 177.4(2) . . . . ?
C10 C11 C12 C13 176.9(2) . . . . ?
C17 C11 C12 C13 -3.3(3) . . . . ?
C4 O1 C13 C12 49.0(2) . . . . ?
C4 O1 C13 C14 -76.0(2) . . . . ?
C7 C12 C13 O1 -35.3(3) . . . . ?
C11 C12 C13 O1 145.5(2) . . . . ?
C7 C12 C13 C14 87.9(3) . . . . ?
C11 C12 C13 C14 -91.4(3) . . . . ?
O1 C13 C14 C15 -56.9(2) . . . . ?
C12 C13 C14 C15 178.5(2) . . . . ?
C16 O2 C15 O3 1.3(4) . . . . ?
C16 O2 C15 C14 -176.3(2) . . . . ?
C13 C14 C15 O3 -65.4(3) . . . . ?
C13 C14 C15 O2 112.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.100
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CCl4'
