# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_16120
_database_code_depnum_ccdc_archive 'CCDC 2013356'
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 I O2, B F4'
_chemical_formula_sum            'C16 H18 B F4 I O2'
_chemical_formula_weight         456.01

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4922(19)
_cell_length_b                   10.184(3)
_cell_length_c                   11.624(3)
_cell_angle_alpha                87.810(4)
_cell_angle_beta                 75.567(4)
_cell_angle_gamma                79.756(4)
_cell_volume                     845.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    896
_cell_measurement_theta_min      2.851
_cell_measurement_theta_max      28.038

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    1.941
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.534
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
;
absoprtion correction based on 5511 reflections(SADABS);Rint 0.0866 before
correction and 0.0323 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6586
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3290
_reflns_number_gt                3151
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0478P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3290
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 0.63716(2) 0.612657(15) 0.709791(13) 0.02116(8) Uani 1 1 d . . .
O1 O 0.3093(3) 0.7472(2) 0.79960(19) 0.0298(5) Uani 1 1 d . . .
H1 H 0.2303 0.7906 0.7661 0.045 Uiso 1 1 calc R . .
O2 O 1.4485(3) 0.30204(19) 0.55875(18) 0.0251(4) Uani 1 1 d . . .
C1 C 0.6047(4) 0.6409(3) 0.8952(2) 0.0197(5) Uani 1 1 d . . .
C2 C 0.7376(4) 0.5651(3) 0.9440(3) 0.0224(6) Uani 1 1 d . . .
H2 H 0.8344 0.5016 0.8973 0.027 Uiso 1 1 calc R . .
C3 C 0.7267(4) 0.5838(3) 1.0646(3) 0.0264(6) Uani 1 1 d . . .
H3 H 0.8155 0.5318 1.1012 0.032 Uiso 1 1 calc R . .
C4 C 0.5869(4) 0.6778(3) 1.1294(3) 0.0270(6) Uani 1 1 d . . .
H4 H 0.5816 0.6927 1.2105 0.032 Uiso 1 1 calc R . .
C5 C 0.4535(4) 0.7511(3) 1.0776(3) 0.0250(6) Uani 1 1 d . . .
H5 H 0.3578 0.8154 1.1241 0.030 Uiso 1 1 calc R . .
C6 C 0.4564(4) 0.7325(3) 0.9581(2) 0.0193(5) Uani 1 1 d . . .
C7 C 0.3040(4) 0.8153(3) 0.9072(2) 0.0223(6) Uani 1 1 d . . .
C8 C 0.3451(4) 0.9562(3) 0.8796(3) 0.0321(7) Uani 1 1 d . . .
H8A H 0.4691 0.9516 0.8250 0.048 Uiso 1 1 calc R . .
H8B H 0.3424 1.0008 0.9534 0.048 Uiso 1 1 calc R . .
H8C H 0.2502 1.0068 0.8426 0.048 Uiso 1 1 calc R . .
C9 C 0.1117(4) 0.8166(3) 0.9901(3) 0.0291(6) Uani 1 1 d . . .
H9A H 0.0157 0.8631 0.9519 0.044 Uiso 1 1 calc R . .
H9B H 0.1036 0.8628 1.0641 0.044 Uiso 1 1 calc R . .
H9C H 0.0917 0.7247 1.0077 0.044 Uiso 1 1 calc R . .
C10 C 0.9092(4) 0.5042(3) 0.6694(2) 0.0212(5) Uani 1 1 d . . .
C11 C 0.9370(4) 0.3653(3) 0.6685(2) 0.0238(6) Uani 1 1 d . . .
H11 H 0.8334 0.3201 0.6927 0.029 Uiso 1 1 calc R . .
C12 C 1.1167(4) 0.2938(3) 0.6319(2) 0.0235(6) Uani 1 1 d . . .
H12 H 1.1372 0.1990 0.6304 0.028 Uiso 1 1 calc R . .
C13 C 1.2669(4) 0.3614(3) 0.5975(2) 0.0205(5) Uani 1 1 d . . .
C14 C 1.2373(4) 0.5007(3) 0.5976(2) 0.0228(6) Uani 1 1 d . . .
H14 H 1.3407 0.5462 0.5728 0.027 Uiso 1 1 calc R . .
C15 C 1.0573(4) 0.5729(3) 0.6337(2) 0.0230(6) Uani 1 1 d . . .
H15 H 1.0360 0.6677 0.6339 0.028 Uiso 1 1 calc R . .
C16 C 1.4890(5) 0.1579(3) 0.5509(3) 0.0326(7) Uani 1 1 d . . .
H16A H 1.4446 0.1202 0.6295 0.049 Uiso 1 1 calc R . .
H16B H 1.6243 0.1282 0.5226 0.049 Uiso 1 1 calc R . .
H16C H 1.4254 0.1277 0.4953 0.049 Uiso 1 1 calc R . .
B1 B 0.9043(5) 0.9438(3) 0.6930(3) 0.0253(7) Uani 1 1 d . . .
F1 F 1.0999(3) 0.9118(2) 0.66939(18) 0.0463(5) Uani 1 1 d . . .
F2 F 0.8456(3) 0.8968(2) 0.6030(2) 0.0536(6) Uani 1 1 d . . .
F3 F 0.8493(3) 1.07910(18) 0.7031(2) 0.0496(5) Uani 1 1 d . . .
F4 F 0.8306(3) 0.8826(2) 0.79834(19) 0.0535(6) 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 C10 2.087(3) . ?
I1 C1 2.132(3) . ?
O1 C7 1.441(3) . ?
O1 H1 0.8400 . ?
O2 C13 1.357(3) . ?
O2 C16 1.446(3) . ?
C1 C2 1.372(4) . ?
C1 C6 1.385(4) . ?
C2 C3 1.402(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.524(4) . ?
C7 C9 1.519(4) . ?
C7 C8 1.526(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.385(4) . ?
C10 C11 1.393(4) . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.397(4) . ?
C14 C15 1.387(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
B1 F2 1.364(4) . ?
B1 F3 1.367(4) . ?
B1 F4 1.386(4) . ?
B1 F1 1.402(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
C10 I1 C1 98.35(10) . . ?
C7 O1 H1 109.5 . . ?
C13 O2 C16 117.8(2) . . ?
C2 C1 C6 124.2(3) . . ?
C2 C1 I1 116.1(2) . . ?
C6 C1 I1 119.65(19) . . ?
C1 C2 C3 118.3(3) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 H2 120.8 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 115.7(3) . . ?
C1 C6 C7 125.4(2) . . ?
C5 C6 C7 118.8(2) . . ?
O1 C7 C9 107.6(2) . . ?
O1 C7 C6 105.4(2) . . ?
C9 C7 C6 111.2(2) . . ?
O1 C7 C8 110.4(2) . . ?
C9 C7 C8 111.7(2) . . ?
C6 C7 C8 110.3(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 121.6(3) . . ?
C15 C10 I1 118.6(2) . . ?
C11 C10 I1 119.6(2) . . ?
C12 C11 C10 119.5(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
O2 C13 C12 124.8(2) . . ?
O2 C13 C14 114.7(2) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C10 C15 C14 118.8(2) . . ?
C10 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
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 . . ?
F2 B1 F3 110.0(3) . . ?
F2 B1 F4 109.6(3) . . ?
F3 B1 F4 110.3(3) . . ?
F2 B1 F1 109.4(3) . . ?
F3 B1 F1 109.8(3) . . ?
F4 B1 F1 107.8(3) . . ?

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
C10 I1 C1 C2 -12.6(2) . . . . ?
C10 I1 C1 C6 166.8(2) . . . . ?
C6 C1 C2 C3 -2.0(4) . . . . ?
I1 C1 C2 C3 177.50(19) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C2 C3 C4 C5 2.0(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C2 C1 C6 C5 3.7(4) . . . . ?
I1 C1 C6 C5 -175.77(19) . . . . ?
C2 C1 C6 C7 -178.3(3) . . . . ?
I1 C1 C6 C7 2.3(4) . . . . ?
C4 C5 C6 C1 -2.6(4) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C1 C6 C7 O1 19.3(4) . . . . ?
C5 C6 C7 O1 -162.7(2) . . . . ?
C1 C6 C7 C9 135.5(3) . . . . ?
C5 C6 C7 C9 -46.5(3) . . . . ?
C1 C6 C7 C8 -99.9(3) . . . . ?
C5 C6 C7 C8 78.1(3) . . . . ?
C1 I1 C10 C15 -91.3(2) . . . . ?
C1 I1 C10 C11 94.5(2) . . . . ?
C15 C10 C11 C12 0.5(4) . . . . ?
I1 C10 C11 C12 174.6(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C16 O2 C13 C12 0.9(4) . . . . ?
C16 O2 C13 C14 -177.1(2) . . . . ?
C11 C12 C13 O2 -179.1(3) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?
O2 C13 C14 C15 179.1(2) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C11 C10 C15 C14 -0.7(4) . . . . ?
I1 C10 C15 C14 -174.9(2) . . . . ?
C13 C14 C15 C10 0.1(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
O1 H1 F1 0.84 1.94 2.759(3) 165.7 1_455

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.104


####################################################################### 
# 
# 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_17098
_database_code_depnum_ccdc_archive 'CCDC 2013359'
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 I O2, B F4'
_chemical_formula_sum            'C21 H20 B F4 I O2'
_chemical_formula_weight         518.08

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.965(2)
_cell_length_b                   11.911(2)
_cell_length_c                   13.389(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.163(3)
_cell_angle_gamma                90.00
_cell_volume                     2021.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    968
_cell_measurement_theta_min      2.998
_cell_measurement_theta_max      28.208

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    1.635
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absoprtion correction based on 9945 reflections(SADABS);Rint 0.0783 before
correction and 0.0283 after.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15347
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3974
_reflns_number_gt                3547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0409P)²+0.6206P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3974
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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 0.277975(14) 0.866617(16) 0.108836(15) 0.02979(8) Uani 1 1 d . . .
O1 O 0.40877(15) 0.70782(16) 0.18152(15) 0.0273(4) Uani 1 1 d . . .
H1 H 0.3587 0.6763 0.1413 0.041 Uiso 1 1 calc R . .
O2 O -0.02338(18) 1.21888(19) -0.13572(17) 0.0402(6) Uani 1 1 d . . .
C1 C 0.3906(2) 0.8548(2) 0.0138(2) 0.0239(6) Uani 1 1 d . . .
C2 C 0.3739(2) 0.9233(3) -0.0717(2) 0.0298(7) Uani 1 1 d . . .
H2 H 0.3175 0.9757 -0.0836 0.036 Uiso 1 1 calc R . .
C3 C 0.4402(2) 0.9145(3) -0.1394(2) 0.0318(7) Uani 1 1 d . . .
H3 H 0.4306 0.9616 -0.1979 0.038 Uiso 1 1 calc R . .
C4 C 0.5209(2) 0.8363(3) -0.1213(2) 0.0323(7) Uani 1 1 d . . .
H4 H 0.5652 0.8277 -0.1690 0.039 Uiso 1 1 calc R . .
C5 C 0.5376(2) 0.7707(2) -0.0341(2) 0.0276(6) Uani 1 1 d . . .
H5 H 0.5943 0.7185 -0.0226 0.033 Uiso 1 1 calc R . .
C6 C 0.4738(2) 0.7787(2) 0.0372(2) 0.0231(6) Uani 1 1 d . . .
C7 C 0.5003(2) 0.7099(2) 0.1366(2) 0.0231(6) Uani 1 1 d . . .
C8 C 0.5305(3) 0.5903(3) 0.1175(2) 0.0314(7) Uani 1 1 d . . .
H8A H 0.5516 0.5509 0.1829 0.047 Uiso 1 1 calc R . .
H8B H 0.5896 0.5907 0.0823 0.047 Uiso 1 1 calc R . .
H8C H 0.4700 0.5519 0.0750 0.047 Uiso 1 1 calc R . .
C9 C 0.5877(2) 0.7704(2) 0.2130(2) 0.0252(6) Uani 1 1 d . . .
C10 C 0.5666(2) 0.8254(2) 0.2974(2) 0.0290(6) Uani 1 1 d . . .
H10 H 0.4967 0.8267 0.3086 0.035 Uiso 1 1 calc R . .
C11 C 0.6477(3) 0.8789(2) 0.3662(2) 0.0360(8) Uani 1 1 d . . .
H11 H 0.6325 0.9172 0.4237 0.043 Uiso 1 1 calc R . .
C12 C 0.7491(3) 0.8765(3) 0.3512(3) 0.0411(8) Uani 1 1 d . . .
H12 H 0.8042 0.9118 0.3989 0.049 Uiso 1 1 calc R . .
C13 C 0.7710(3) 0.8229(3) 0.2669(3) 0.0446(8) Uani 1 1 d . . .
H13 H 0.8412 0.8219 0.2562 0.053 Uiso 1 1 calc R . .
C14 C 0.6908(2) 0.7704(3) 0.1977(2) 0.0374(8) Uani 1 1 d . . .
H14 H 0.7062 0.7342 0.1394 0.045 Uiso 1 1 calc R . .
C15 C 0.1823(2) 0.9889(2) 0.0238(2) 0.0272(6) Uani 1 1 d . . .
C16 C 0.1087(2) 0.9571(2) -0.0627(2) 0.0293(7) Uani 1 1 d . . .
H16 H 0.1050 0.8815 -0.0857 0.035 Uiso 1 1 calc R . .
C17 C 0.0416(2) 1.0363(3) -0.1141(2) 0.0304(7) Uani 1 1 d . . .
H17 H -0.0097 1.0158 -0.1729 0.036 Uiso 1 1 calc R . .
C18 C 0.0484(2) 1.1480(2) -0.0800(2) 0.0283(6) Uani 1 1 d . . .
C19 C 0.1224(2) 1.1791(3) 0.0051(2) 0.0286(6) Uani 1 1 d . . .
H19 H 0.1272 1.2550 0.0274 0.034 Uiso 1 1 calc R . .
C20 C 0.1900(2) 1.0983(3) 0.0582(2) 0.0294(6) Uani 1 1 d . . .
H20 H 0.2409 1.1183 0.1176 0.035 Uiso 1 1 calc R . .
C21 C -0.0179(4) 1.3341(3) -0.1056(3) 0.0549(11) Uani 1 1 d . . .
H21A H -0.0270 1.3401 -0.0350 0.082 Uiso 1 1 calc R . .
H21B H -0.0739 1.3764 -0.1507 0.082 Uiso 1 1 calc R . .
H21C H 0.0510 1.3650 -0.1105 0.082 Uiso 1 1 calc R . .
B1 B 0.2531(3) 0.4340(3) 0.1276(3) 0.0288(7) Uani 1 1 d . . .
F1 F 0.28445(17) 0.33261(18) 0.17519(16) 0.0492(5) Uani 1 1 d . . .
F2 F 0.28646(16) 0.44001(19) 0.03754(15) 0.0520(6) Uani 1 1 d . . .
F3 F 0.29604(18) 0.52061(19) 0.19369(18) 0.0605(6) Uani 1 1 d . . .
F4 F 0.14500(14) 0.43981(16) 0.11073(17) 0.0473(5) 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 C15 2.088(3) . ?
I1 C1 2.134(3) . ?
O1 C7 1.439(3) . ?
O1 H1 0.8400 . ?
O2 C18 1.357(4) . ?
O2 C21 1.428(4) . ?
C1 C2 1.386(4) . ?
C1 C6 1.392(4) . ?
C2 C3 1.377(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.539(4) . ?
C7 C8 1.513(4) . ?
C7 C9 1.537(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.382(4) . ?
C9 C14 1.393(4) . ?
C10 C11 1.398(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.388(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.378(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.367(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(4) . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 F2 1.366(4) . ?
B1 F4 1.374(4) . ?
B1 F1 1.386(4) . ?
B1 F3 1.396(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
C15 I1 C1 97.12(11) . . ?
C7 O1 H1 109.5 . . ?
C18 O2 C21 117.1(3) . . ?
C2 C1 C6 123.2(3) . . ?
C2 C1 I1 116.5(2) . . ?
C6 C1 I1 120.2(2) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 122.0(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 115.7(3) . . ?
C1 C6 C7 124.2(2) . . ?
C5 C6 C7 120.0(2) . . ?
O1 C7 C8 108.7(2) . . ?
O1 C7 C9 106.7(2) . . ?
C8 C7 C9 111.9(2) . . ?
O1 C7 C6 108.5(2) . . ?
C8 C7 C6 112.0(2) . . ?
C9 C7 C6 108.9(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.7(3) . . ?
C10 C9 C7 121.4(3) . . ?
C14 C9 C7 119.9(3) . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C20 C15 C16 121.6(3) . . ?
C20 C15 I1 119.0(2) . . ?
C16 C15 I1 119.3(2) . . ?
C17 C16 C15 119.0(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
O2 C18 C19 124.4(3) . . ?
O2 C18 C17 114.9(3) . . ?
C19 C18 C17 120.6(3) . . ?
C18 C19 C20 119.4(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C15 C20 C19 119.3(3) . . ?
C15 C20 H20 120.4 . . ?
C19 C20 H20 120.4 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 B1 F4 110.8(3) . . ?
F2 B1 F1 109.6(3) . . ?
F4 B1 F1 108.0(3) . . ?
F2 B1 F3 111.3(3) . . ?
F4 B1 F3 108.9(3) . . ?
F1 B1 F3 108.2(3) . . ?

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
C15 I1 C1 C2 -0.3(2) . . . . ?
C15 I1 C1 C6 -178.4(2) . . . . ?
C6 C1 C2 C3 2.0(5) . . . . ?
I1 C1 C2 C3 -176.0(2) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C2 C3 C4 C5 -2.5(5) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
C2 C1 C6 C5 -3.3(4) . . . . ?
I1 C1 C6 C5 174.7(2) . . . . ?
C2 C1 C6 C7 174.0(3) . . . . ?
I1 C1 C6 C7 -8.0(4) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C4 C5 C6 C7 -175.7(3) . . . . ?
C1 C6 C7 O1 19.2(4) . . . . ?
C5 C6 C7 O1 -163.7(2) . . . . ?
C1 C6 C7 C8 139.1(3) . . . . ?
C5 C6 C7 C8 -43.8(3) . . . . ?
C1 C6 C7 C9 -96.6(3) . . . . ?
C5 C6 C7 C9 80.5(3) . . . . ?
O1 C7 C9 C10 -9.7(3) . . . . ?
C8 C7 C9 C10 -128.5(3) . . . . ?
C6 C7 C9 C10 107.2(3) . . . . ?
O1 C7 C9 C14 170.3(3) . . . . ?
C8 C7 C9 C14 51.5(4) . . . . ?
C6 C7 C9 C14 -72.8(3) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C7 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 1.2(5) . . . . ?
C11 C12 C13 C14 -0.6(5) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
C10 C9 C14 C13 1.2(5) . . . . ?
C7 C9 C14 C13 -178.8(3) . . . . ?
C1 I1 C15 C20 -102.7(2) . . . . ?
C1 I1 C15 C16 80.7(2) . . . . ?
C20 C15 C16 C17 -0.7(4) . . . . ?
I1 C15 C16 C17 175.7(2) . . . . ?
C15 C16 C17 C18 0.7(4) . . . . ?
C21 O2 C18 C19 2.7(5) . . . . ?
C21 O2 C18 C17 -178.4(3) . . . . ?
C16 C17 C18 O2 -178.8(3) . . . . ?
C16 C17 C18 C19 0.1(5) . . . . ?
O2 C18 C19 C20 178.0(3) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C16 C15 C20 C19 0.0(5) . . . . ?
I1 C15 C20 C19 -176.5(2) . . . . ?
C18 C19 C20 C15 0.8(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
O1 H1 F3 0.84 2.20 2.690(3) 117.4 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_17107
_database_code_depnum_ccdc_archive 'CCDC 2013358'
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 I O, B F4'
_chemical_formula_sum            'C21 H18 B F4 I O'
_chemical_formula_weight         500.06

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.995(5)
_cell_length_b                   14.196(6)
_cell_length_c                   22.602(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3849(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    982
_cell_measurement_theta_min      2.860
_cell_measurement_theta_max      26.466

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1968
_exptl_absorpt_coefficient_mu    1.710
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.263
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absorption correction based on 12962 reflections(SADABS);Rint 0.1595 before
correction and 0.0678 after.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27920
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.80
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3778
_reflns_number_gt                3071
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0357P)²+3.8042P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3778
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.31197(2) 0.158197(17) 0.614226(11) 0.02484(10) Uani 1 1 d . . .
O1 O 0.5098(3) 0.1745(2) 0.86690(12) 0.0331(7) Uani 1 1 d . . .
C1 C 0.4078(3) 0.0391(3) 0.58961(16) 0.0210(8) Uani 1 1 d . . .
C2 C 0.5205(3) 0.0535(3) 0.58098(16) 0.0238(9) Uani 1 1 d . . .
H2 H 0.5528 0.1141 0.5855 0.029 Uiso 1 1 calc R . .
C3 C 0.5844(3) -0.0235(3) 0.56555(16) 0.0274(9) Uani 1 1 d . . .
H3 H 0.6627 -0.0168 0.5610 0.033 Uiso 1 1 calc R . .
C4 C 0.5351(4) -0.1099(3) 0.55680(17) 0.0292(10) Uani 1 1 d . . .
H4 H 0.5794 -0.1620 0.5449 0.035 Uiso 1 1 calc R . .
C5 C 0.4215(4) -0.1215(3) 0.56509(16) 0.0261(9) Uani 1 1 d . . .
H5 H 0.3892 -0.1817 0.5587 0.031 Uiso 1 1 calc R . .
C6 C 0.3539(3) -0.0471(3) 0.58252(15) 0.0216(8) Uani 1 1 d . . .
C7 C 0.2329(3) -0.0615(3) 0.59529(17) 0.0239(9) Uani 1 1 d . . .
C8 C 0.1604(4) -0.0653(3) 0.55104(19) 0.0391(12) Uani 1 1 d . . .
H8A H 0.0835 -0.0753 0.5590 0.047 Uiso 1 1 calc R . .
H8B H 0.1853 -0.0580 0.5114 0.047 Uiso 1 1 calc R . .
C9 C 0.2024(3) -0.0722(3) 0.65870(16) 0.0218(8) Uani 1 1 d . . .
C10 C 0.0968(3) -0.0475(3) 0.67937(19) 0.0295(9) Uani 1 1 d . . .
H10 H 0.0426 -0.0249 0.6523 0.035 Uiso 1 1 calc R . .
C11 C 0.0698(4) -0.0554(3) 0.73856(18) 0.0321(10) Uani 1 1 d . . .
H11 H -0.0021 -0.0372 0.7520 0.039 Uiso 1 1 calc R . .
C12 C 0.1477(4) -0.0900(3) 0.77847(18) 0.0305(10) Uani 1 1 d . . .
H12 H 0.1289 -0.0966 0.8191 0.037 Uiso 1 1 calc R . .
C13 C 0.2517(4) -0.1143(3) 0.75891(18) 0.0287(9) Uani 1 1 d . . .
H13 H 0.3049 -0.1382 0.7862 0.034 Uiso 1 1 calc R . .
C14 C 0.2804(3) -0.1046(3) 0.69964(17) 0.0248(9) Uani 1 1 d . . .
H14 H 0.3537 -0.1201 0.6870 0.030 Uiso 1 1 calc R . .
C15 C 0.3745(3) 0.1657(3) 0.70082(16) 0.0219(8) Uani 1 1 d . . .
C16 C 0.4782(3) 0.2052(3) 0.70949(17) 0.0242(9) Uani 1 1 d . . .
H16 H 0.5191 0.2313 0.6774 0.029 Uiso 1 1 calc R . .
C17 C 0.5208(3) 0.2056(3) 0.76640(17) 0.0246(9) Uani 1 1 d . . .
H17 H 0.5930 0.2308 0.7735 0.030 Uiso 1 1 calc R . .
C18 C 0.4595(3) 0.1695(3) 0.81312(17) 0.0257(9) Uani 1 1 d . . .
C19 C 0.3548(3) 0.1302(3) 0.80369(17) 0.0262(9) Uani 1 1 d . . .
H19 H 0.3130 0.1055 0.8358 0.031 Uiso 1 1 calc R . .
C20 C 0.3122(4) 0.1277(3) 0.74641(18) 0.0250(8) Uani 1 1 d . . .
H20 H 0.2414 0.1003 0.7388 0.030 Uiso 1 1 calc R . .
C21 C 0.4496(4) 0.1391(3) 0.91718(18) 0.0363(11) Uani 1 1 d . . .
H21A H 0.3781 0.1720 0.9204 0.054 Uiso 1 1 calc R . .
H21B H 0.4934 0.1498 0.9532 0.054 Uiso 1 1 calc R . .
H21C H 0.4364 0.0715 0.9122 0.054 Uiso 1 1 calc R . .
B1 B 0.1551(4) 0.1802(3) 0.4385(2) 0.0272(10) Uani 1 1 d . . .
F1 F 0.0510(2) 0.21899(17) 0.44778(12) 0.0435(7) Uani 1 1 d . . .
F2 F 0.2114(3) 0.2328(3) 0.39807(14) 0.0680(10) Uani 1 1 d . . .
F3 F 0.2135(2) 0.1784(2) 0.49179(11) 0.0489(7) Uani 1 1 d . . .
F4 F 0.1436(2) 0.0895(2) 0.41812(15) 0.0578(8) 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 C15 2.099(4) . ?
I1 C1 2.118(4) . ?
O1 C18 1.359(5) . ?
O1 C21 1.437(5) . ?
C1 C2 1.381(5) . ?
C1 C6 1.394(5) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(5) . ?
C7 C8 1.327(6) . ?
C7 C9 1.487(5) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C14 1.394(5) . ?
C9 C10 1.395(5) . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.367(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.379(5) . ?
C15 C20 1.382(6) . ?
C16 C17 1.384(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(6) . ?
C19 C20 1.392(6) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
B1 F2 1.360(5) . ?
B1 F4 1.375(5) . ?
B1 F1 1.381(5) . ?
B1 F3 1.394(5) . ?

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
C15 I1 C1 95.26(14) . . ?
C18 O1 C21 117.8(3) . . ?
C2 C1 C6 124.6(4) . . ?
C2 C1 I1 116.8(3) . . ?
C6 C1 I1 118.6(3) . . ?
C3 C2 C1 117.6(4) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.5(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 115.4(4) . . ?
C5 C6 C7 121.2(3) . . ?
C1 C6 C7 123.3(3) . . ?
C8 C7 C9 124.1(4) . . ?
C8 C7 C6 119.8(4) . . ?
C9 C7 C6 116.1(3) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C14 C9 C10 118.0(4) . . ?
C14 C9 C7 120.6(3) . . ?
C10 C9 C7 121.4(3) . . ?
C11 C10 C9 121.2(4) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.0(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.6(4) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.8(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 120.4(4) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C16 C15 C20 122.7(4) . . ?
C16 C15 I1 118.4(3) . . ?
C20 C15 I1 118.8(3) . . ?
C15 C16 C17 117.8(4) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C16 C17 C18 120.7(4) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
O1 C18 C17 115.3(4) . . ?
O1 C18 C19 124.0(4) . . ?
C17 C18 C19 120.7(4) . . ?
C18 C19 C20 119.0(4) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C15 C20 C19 119.0(4) . . ?
C15 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F2 B1 F4 109.8(4) . . ?
F2 B1 F1 109.4(4) . . ?
F4 B1 F1 109.5(4) . . ?
F2 B1 F3 109.9(4) . . ?
F4 B1 F3 108.8(4) . . ?
F1 B1 F3 109.3(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
C15 I1 C1 C2 -72.5(3) . . . . ?
C15 I1 C1 C6 108.3(3) . . . . ?
C6 C1 C2 C3 -1.5(6) . . . . ?
I1 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 2.7(6) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C3 C4 C5 C6 -0.1(6) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 C7 -175.9(3) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
I1 C1 C6 C5 178.6(3) . . . . ?
C2 C1 C6 C7 176.6(4) . . . . ?
I1 C1 C6 C7 -4.2(5) . . . . ?
C5 C6 C7 C8 -80.8(5) . . . . ?
C1 C6 C7 C8 102.2(5) . . . . ?
C5 C6 C7 C9 98.4(4) . . . . ?
C1 C6 C7 C9 -78.6(5) . . . . ?
C8 C7 C9 C14 154.2(4) . . . . ?
C6 C7 C9 C14 -25.0(5) . . . . ?
C8 C7 C9 C10 -27.7(6) . . . . ?
C6 C7 C9 C10 153.1(4) . . . . ?
C14 C9 C10 C11 -0.3(6) . . . . ?
C7 C9 C10 C11 -178.4(4) . . . . ?
C9 C10 C11 C12 -1.2(6) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C9 -1.8(6) . . . . ?
C10 C9 C14 C13 1.8(6) . . . . ?
C7 C9 C14 C13 179.9(4) . . . . ?
C1 I1 C15 C16 78.7(3) . . . . ?
C1 I1 C15 C20 -98.8(3) . . . . ?
C20 C15 C16 C17 0.5(6) . . . . ?
I1 C15 C16 C17 -176.9(3) . . . . ?
C15 C16 C17 C18 -1.7(6) . . . . ?
C21 O1 C18 C17 179.3(3) . . . . ?
C21 O1 C18 C19 -1.7(5) . . . . ?
C16 C17 C18 O1 -179.5(3) . . . . ?
C16 C17 C18 C19 1.5(6) . . . . ?
O1 C18 C19 C20 -179.0(4) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C16 C15 C20 C19 0.9(6) . . . . ?
I1 C15 C20 C19 178.3(3) . . . . ?
C18 C19 C20 C15 -1.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.099

####################################################################### 
# 
# 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_17070
_database_code_depnum_ccdc_archive 'CCDC 2013357'
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 I O, C F3 O3 S'
_chemical_formula_sum            'C22 H18 F3 I O4 S'
_chemical_formula_weight         562.32

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4537(14)
_cell_length_b                   11.6591(19)
_cell_length_c                   12.124(2)
_cell_angle_alpha                66.609(2)
_cell_angle_beta                 87.336(3)
_cell_angle_gamma                76.601(2)
_cell_volume                     1065.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    976
_cell_measurement_theta_min      2.949
_cell_measurement_theta_max      27.949

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_process_details   
; 
absoprtion correction based on 6682 reflections(SADABS);Rint 0.0495 before 
correction and 0.0284 after. 
;


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8303
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         25.99
_reflns_number_total             4139
_reflns_number_gt                3872
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0449P)²+0.1580P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4139
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0735
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.81209(2) 0.820060(16) 0.609430(15) 0.02277(8) Uani 1 1 d . . .
O1 O 1.1870(3) 0.9207(2) 0.9756(2) 0.0341(5) Uani 1 1 d . . .
C1 C 0.9312(3) 0.6293(3) 0.6395(2) 0.0220(6) Uani 1 1 d . . .
C2 C 1.0845(4) 0.6064(3) 0.5955(3) 0.0308(7) Uani 1 1 d . . .
H2 H 1.1364 0.6749 0.5549 0.037 Uiso 1 1 calc R . .
C3 C 1.1600(4) 0.4816(3) 0.6121(3) 0.0356(8) Uani 1 1 d . . .
H3 H 1.2648 0.4637 0.5824 0.043 Uiso 1 1 calc R . .
C4 C 1.0832(4) 0.3833(3) 0.6717(3) 0.0350(8) Uani 1 1 d . . .
H4 H 1.1355 0.2978 0.6826 0.042 Uiso 1 1 calc R . .
C5 C 0.9307(4) 0.4080(3) 0.7157(3) 0.0318(7) Uani 1 1 d . . .
H5 H 0.8804 0.3388 0.7573 0.038 Uiso 1 1 calc R . .
C6 C 0.8492(4) 0.5323(3) 0.7002(3) 0.0232(6) Uani 1 1 d . . .
C7 C 0.6834(4) 0.5611(3) 0.7450(3) 0.0233(6) Uani 1 1 d . . .
C8 C 0.5532(4) 0.5777(3) 0.6784(3) 0.0312(7) Uani 1 1 d . . .
H8A H 0.4473 0.5989 0.7052 0.037 Uiso 1 1 calc R . .
H8B H 0.5659 0.5684 0.6039 0.037 Uiso 1 1 calc R . .
C9 C 0.6732(3) 0.5740(3) 0.8626(3) 0.0220(6) Uani 1 1 d . . .
C10 C 0.5426(4) 0.6573(3) 0.8854(3) 0.0269(6) Uani 1 1 d . . .
H10 H 0.4586 0.7077 0.8248 0.032 Uiso 1 1 calc R . .
C11 C 0.5331(4) 0.6679(3) 0.9956(3) 0.0306(7) Uani 1 1 d . . .
H11 H 0.4421 0.7244 1.0102 0.037 Uiso 1 1 calc R . .
C12 C 0.6548(4) 0.5972(3) 1.0836(3) 0.0297(7) Uani 1 1 d . . .
H12 H 0.6491 0.6065 1.1581 0.036 Uiso 1 1 calc R . .
C13 C 0.7861(4) 0.5122(3) 1.0637(3) 0.0310(7) Uani 1 1 d . . .
H13 H 0.8692 0.4619 1.1252 0.037 Uiso 1 1 calc R . .
C14 C 0.7954(4) 0.5008(3) 0.9535(3) 0.0257(6) Uani 1 1 d . . .
H14 H 0.8855 0.4429 0.9398 0.031 Uiso 1 1 calc R . .
C15 C 0.9513(3) 0.8433(3) 0.7341(3) 0.0229(6) Uani 1 1 d . . .
C16 C 1.0849(4) 0.8965(3) 0.6957(3) 0.0278(6) Uani 1 1 d . . .
H16 H 1.1186 0.9144 0.6159 0.033 Uiso 1 1 calc R . .
C17 C 1.1692(4) 0.9232(3) 0.7748(3) 0.0286(7) Uani 1 1 d . . .
H17 H 1.2613 0.9592 0.7499 0.034 Uiso 1 1 calc R . .
C18 C 1.1167(4) 0.8965(3) 0.8915(3) 0.0276(6) Uani 1 1 d . . .
C19 C 0.9851(4) 0.8400(3) 0.9290(3) 0.0264(6) Uani 1 1 d . . .
H19 H 0.9539 0.8184 1.0098 0.032 Uiso 1 1 calc R . .
C20 C 0.8992(4) 0.8149(3) 0.8506(3) 0.0251(6) Uani 1 1 d . . .
H20 H 0.8070 0.7790 0.8754 0.030 Uiso 1 1 calc R . .
C21 C 1.3061(4) 0.9973(4) 0.9364(3) 0.0396(8) Uani 1 1 d . . .
H21A H 1.4023 0.9497 0.9116 0.059 Uiso 1 1 calc R . .
H21B H 1.3375 1.0167 1.0027 0.059 Uiso 1 1 calc R . .
H21C H 1.2595 1.0777 0.8683 0.059 Uiso 1 1 calc R . .
C22 C 0.3739(4) 0.7945(3) 0.3154(3) 0.0301(7) Uani 1 1 d . . .
F1 F 0.4577(3) 0.7853(2) 0.22253(19) 0.0523(6) Uani 1 1 d . . .
F2 F 0.3791(3) 0.67586(19) 0.39575(19) 0.0454(5) Uani 1 1 d . . .
F3 F 0.2203(3) 0.8497(2) 0.2775(2) 0.0538(6) Uani 1 1 d . . .
S1 S 0.45852(9) 0.88571(7) 0.38056(7) 0.02576(17) Uani 1 1 d . . .
O2 O 0.4488(3) 1.0074(2) 0.2818(2) 0.0370(5) Uani 1 1 d . . .
O3 O 0.6213(3) 0.8086(2) 0.4200(2) 0.0326(5) Uani 1 1 d . . .
O4 O 0.3518(3) 0.8906(3) 0.4752(2) 0.0417(6) 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 C15 2.094(3) . ?
I1 C1 2.108(3) . ?
O1 C18 1.354(4) . ?
O1 C21 1.440(4) . ?
C1 C2 1.387(4) . ?
C1 C6 1.398(4) . ?
C2 C3 1.384(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.493(4) . ?
C7 C8 1.327(4) . ?
C7 C9 1.488(4) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.388(4) . ?
C9 C14 1.401(4) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.387(4) . ?
C15 C20 1.391(4) . ?
C16 C17 1.389(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C19 C20 1.379(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 F3 1.321(4) . ?
C22 F1 1.330(4) . ?
C22 F2 1.331(4) . ?
C22 S1 1.827(3) . ?
S1 O2 1.435(2) . ?
S1 O4 1.437(2) . ?
S1 O3 1.441(2) . ?

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
C15 I1 C1 98.00(11) . . ?
C18 O1 C21 117.4(3) . . ?
C2 C1 C6 123.2(3) . . ?
C2 C1 I1 118.7(2) . . ?
C6 C1 I1 118.1(2) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 116.2(3) . . ?
C5 C6 C7 122.1(3) . . ?
C1 C6 C7 121.6(3) . . ?
C8 C7 C9 123.1(3) . . ?
C8 C7 C6 119.6(3) . . ?
C9 C7 C6 117.3(2) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C10 C9 C14 118.4(3) . . ?
C10 C9 C7 121.2(3) . . ?
C14 C9 C7 120.4(3) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.1(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C9 C14 H14 119.7 . . ?
C16 C15 C20 121.9(3) . . ?
C16 C15 I1 119.0(2) . . ?
C20 C15 I1 118.9(2) . . ?
C15 C16 C17 119.5(3) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
O1 C18 C19 115.2(3) . . ?
O1 C18 C17 124.4(3) . . ?
C19 C18 C17 120.3(3) . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C15 118.2(3) . . ?
C19 C20 H20 120.9 . . ?
C15 C20 H20 120.9 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F3 C22 F1 108.2(3) . . ?
F3 C22 F2 107.6(3) . . ?
F1 C22 F2 107.7(3) . . ?
F3 C22 S1 111.3(2) . . ?
F1 C22 S1 110.8(2) . . ?
F2 C22 S1 111.1(2) . . ?
O2 S1 O4 114.37(15) . . ?
O2 S1 O3 114.98(14) . . ?
O4 S1 O3 115.26(15) . . ?
O2 S1 C22 103.56(15) . . ?
O4 S1 C22 103.56(15) . . ?
O3 S1 C22 102.79(14) . . ?

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
C15 I1 C1 C2 -74.1(2) . . . . ?
C15 I1 C1 C6 107.7(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
I1 C1 C2 C3 -177.9(2) . . . . ?
C1 C2 C3 C4 -0.3(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C4 C5 C6 C1 -0.8(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C2 C1 C6 C5 0.4(4) . . . . ?
I1 C1 C6 C5 178.5(2) . . . . ?
C2 C1 C6 C7 -179.3(3) . . . . ?
I1 C1 C6 C7 -1.2(4) . . . . ?
C5 C6 C7 C8 -84.1(4) . . . . ?
C1 C6 C7 C8 95.6(4) . . . . ?
C5 C6 C7 C9 97.9(3) . . . . ?
C1 C6 C7 C9 -82.4(3) . . . . ?
C8 C7 C9 C10 -30.2(4) . . . . ?
C6 C7 C9 C10 147.7(3) . . . . ?
C8 C7 C9 C14 149.1(3) . . . . ?
C6 C7 C9 C14 -33.0(4) . . . . ?
C14 C9 C10 C11 0.0(4) . . . . ?
C7 C9 C10 C11 179.4(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 -1.6(5) . . . . ?
C11 C12 C13 C14 1.3(5) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C10 C9 C14 C13 -0.4(4) . . . . ?
C7 C9 C14 C13 -179.7(3) . . . . ?
C1 I1 C15 C16 93.4(2) . . . . ?
C1 I1 C15 C20 -91.8(2) . . . . ?
C20 C15 C16 C17 -0.5(5) . . . . ?
I1 C15 C16 C17 174.1(2) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C21 O1 C18 C19 -170.3(3) . . . . ?
C21 O1 C18 C17 10.5(5) . . . . ?
C16 C17 C18 O1 -178.7(3) . . . . ?
C16 C17 C18 C19 2.1(5) . . . . ?
O1 C18 C19 C20 177.6(3) . . . . ?
C17 C18 C19 C20 -3.1(5) . . . . ?
C18 C19 C20 C15 2.2(4) . . . . ?
C16 C15 C20 C19 -0.5(5) . . . . ?
I1 C15 C20 C19 -175.1(2) . . . . ?
F3 C22 S1 O2 -62.2(3) . . . . ?
F1 C22 S1 O2 58.3(2) . . . . ?
F2 C22 S1 O2 178.0(2) . . . . ?
F3 C22 S1 O4 57.5(3) . . . . ?
F1 C22 S1 O4 177.9(2) . . . . ?
F2 C22 S1 O4 -62.4(3) . . . . ?
F3 C22 S1 O3 177.8(2) . . . . ?
F1 C22 S1 O3 -61.7(2) . . . . ?
F2 C22 S1 O3 57.9(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.762
_refine_diff_density_rms         0.101


####################################################################### 
# 
# 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_18089
_database_code_depnum_ccdc_archive 'CCDC 2013360'
_audit_update_record             
;
2020-07-01 deposited with the CCDC.	2020-07-23 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         'C21 H18 I O, C7 H7 O3 S'
_chemical_formula_sum            'C28 H25 I O4 S'
_chemical_formula_weight         584.44

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'
S S 0.1246 0.1234 '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                   13.148(3)
_cell_length_b                   13.175(2)
_cell_length_c                   16.115(3)
_cell_angle_alpha                83.966(3)
_cell_angle_beta                 86.472(3)
_cell_angle_gamma                60.099(3)
_cell_volume                     2406.2(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    996
_cell_measurement_theta_min      2.969
_cell_measurement_theta_max      26.667

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_F_000             1176
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    1.451
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   
;
absoprtion correction based on 10449 reflections(SADABS);Rint 0.0536 before
correction and 0.0318 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18860
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.787
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             9333
_reflns_number_gt                7405
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0279P)²] 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         9333
_refine_ls_number_parameters     617
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0750
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_restrained_S_all      0.947
_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 0.75821(2) 0.22518(2) 0.23871(2) 0.02453(7) Uani 1 1 d . . . . .
O1 O 0.9450(3) 0.3636(3) 0.52479(19) 0.0508(9) Uani 1 1 d . . . . .
C1 C 0.9107(3) 0.0593(3) 0.2450(2) 0.0223(8) Uani 1 1 d . . . . .
C2 C 1.0048(3) 0.0495(3) 0.1977(2) 0.0315(9) Uani 1 1 d . . . . .
H2 H 0.998566 0.114752 0.162347 0.038 Uiso 1 1 calc R U . . .
C3 C 1.1089(3) -0.0564(4) 0.2018(3) 0.0355(10) Uani 1 1 d . . . . .
H3 H 1.174859 -0.064651 0.169143 0.043 Uiso 1 1 calc R U . . .
C4 C 1.1161(4) -0.1491(4) 0.2534(3) 0.0390(11) Uani 1 1 d . . . . .
H4 H 1.187970 -0.221425 0.257033 0.047 Uiso 1 1 calc R U . . .
C5 C 1.0207(4) -0.1392(3) 0.3001(3) 0.0350(10) Uani 1 1 d . . . . .
H5 H 1.027843 -0.204951 0.335242 0.042 Uiso 1 1 calc R U . . .
C6 C 0.9137(3) -0.0342(3) 0.2966(2) 0.0266(9) Uani 1 1 d . . . . .
C7 C 0.8091(3) -0.0239(3) 0.3441(2) 0.0292(9) Uani 1 1 d . . . . .
C8 C 0.7294(4) -0.0335(4) 0.3057(3) 0.0409(11) Uani 1 1 d . . . . .
H8A H 0.660333 -0.023585 0.334760 0.049 Uiso 1 1 calc R U . . .
H8B H 0.740803 -0.050436 0.248923 0.049 Uiso 1 1 calc R U . . .
C9 C 0.7963(3) 0.0022(4) 0.4322(2) 0.0301(9) Uani 1 1 d . . . . .
C10 C 0.6867(4) 0.0783(4) 0.4646(3) 0.0438(12) Uani 1 1 d . . . . .
H10 H 0.619843 0.112621 0.429774 0.053 Uiso 1 1 calc R U . . .
C11 C 0.6736(4) 0.1049(5) 0.5468(3) 0.0545(14) Uani 1 1 d . . . . .
H11 H 0.598002 0.157517 0.567692 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7693(4) 0.0557(5) 0.5987(3) 0.0534(14) Uani 1 1 d . . . . .
H12 H 0.760174 0.073522 0.655177 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8781(4) -0.0195(5) 0.5671(3) 0.0520(13) Uani 1 1 d . . . . .
H13 H 0.944350 -0.056038 0.602557 0.062 Uiso 1 1 calc R U . . .
C14 C 0.8916(4) -0.0422(4) 0.4844(3) 0.0416(11) Uani 1 1 d . . . . .
H14 H 0.968193 -0.089576 0.462626 0.050 Uiso 1 1 calc R U . . .
C15 C 0.8154(3) 0.2834(3) 0.3328(2) 0.0261(9) Uani 1 1 d . . . . .
C16 C 0.9072(4) 0.3043(4) 0.3158(3) 0.0340(10) Uani 1 1 d . . . . .
H16 H 0.939432 0.299207 0.260980 0.041 Uiso 1 1 calc R U . . .
C17 C 0.9522(4) 0.3329(4) 0.3788(3) 0.0405(11) Uani 1 1 d . . . . .
H17 H 1.015984 0.347104 0.367672 0.049 Uiso 1 1 calc R U . . .
C18 C 0.9045(4) 0.3407(4) 0.4577(3) 0.0367(10) Uani 1 1 d . . . . .
C19 C 0.8109(4) 0.3223(4) 0.4739(3) 0.0367(10) Uani 1 1 d . . . . .
H19 H 0.777688 0.329008 0.528421 0.044 Uiso 1 1 calc R U . . .
C20 C 0.7648(4) 0.2939(3) 0.4109(3) 0.0342(10) Uani 1 1 d . . . . .
H20 H 0.699533 0.281897 0.421574 0.041 Uiso 1 1 calc R U . . .
C21 C 1.0610(5) 0.3470(5) 0.5192(3) 0.0730(17) Uani 1 1 d . . . . .
H21A H 1.115698 0.268183 0.502373 0.110 Uiso 1 1 calc R U . . .
H21B H 1.083835 0.355609 0.573695 0.110 Uiso 1 1 calc R U . . .
H21C H 1.063222 0.405934 0.477736 0.110 Uiso 1 1 calc R U . . .
C22 C 0.4375(3) 0.4138(3) 0.3563(2) 0.0270(9) Uani 1 1 d . . . . .
C23 C 0.4146(4) 0.4254(4) 0.4402(3) 0.0426(11) Uani 1 1 d . . . . .
H23 H 0.415850 0.487137 0.464975 0.051 Uiso 1 1 calc R U . . .
C24 C 0.3898(4) 0.3468(4) 0.4885(3) 0.0513(13) Uani 1 1 d . . . . .
H24 H 0.374846 0.354396 0.546600 0.062 Uiso 1 1 calc R U . . .
C25 C 0.3865(4) 0.2577(4) 0.4530(3) 0.0485(13) Uani 1 1 d . . . . .
C26 C 0.4109(3) 0.2470(4) 0.3689(3) 0.0382(11) Uani 1 1 d . . . . .
H26 H 0.410241 0.185093 0.344041 0.046 Uiso 1 1 calc R U . . .
C27 C 0.4363(3) 0.3238(3) 0.3201(3) 0.0314(9) Uani 1 1 d . . . . .
H27 H 0.452735 0.315180 0.262219 0.038 Uiso 1 1 calc R U . . .
C28 C 0.3667(5) 0.1673(4) 0.5064(4) 0.0751(18) Uani 1 1 d . . . . .
H28A H 0.337096 0.131214 0.471568 0.113 Uiso 1 1 calc R U . . .
H28B H 0.309236 0.205697 0.550486 0.113 Uiso 1 1 calc R U . . .
H28C H 0.440965 0.106607 0.531594 0.113 Uiso 1 1 calc R U . . .
S1 S 0.46766(9) 0.51474(8) 0.29301(6) 0.0279(2) Uani 1 1 d . . . . .
O2 O 0.3621(2) 0.5904(2) 0.24482(16) 0.0303(6) Uani 1 1 d . . . . .
O3 O 0.4963(3) 0.5757(3) 0.34749(19) 0.0497(8) Uani 1 1 d . . . . .
O4 O 0.5642(2) 0.4420(2) 0.23862(17) 0.0349(7) Uani 1 1 d . . . . .
I1A I 0.35082(2) 0.49115(2) 0.09918(2) 0.02152(7) Uani 1 1 d . . . . .
O1A O 0.2591(2) 0.2975(2) -0.20377(17) 0.0346(7) Uani 1 1 d . . . . .
C1A C 0.1787(3) 0.6370(3) 0.0993(2) 0.0210(8) Uani 1 1 d . . . . .
C2A C 0.1598(3) 0.7314(3) 0.0434(2) 0.0267(9) Uani 1 1 d . . . . .
H2A H 0.221525 0.729779 0.008641 0.032 Uiso 1 1 calc R U . . .
C3A C 0.0485(3) 0.8285(3) 0.0394(2) 0.0291(9) Uani 1 1 d . . . . .
H3A H 0.033290 0.894272 0.001106 0.035 Uiso 1 1 calc R U . . .
C4A C -0.0403(3) 0.8310(3) 0.0902(2) 0.0311(9) Uani 1 1 d . . . . .
H4A H -0.116390 0.898369 0.087366 0.037 Uiso 1 1 calc R U . . .
C5A C -0.0186(3) 0.7349(3) 0.1457(2) 0.0279(9) Uani 1 1 d . . . . .
H5A H -0.080541 0.736920 0.180393 0.033 Uiso 1 1 calc R U . . .
C6A C 0.0923(3) 0.6351(3) 0.1516(2) 0.0224(8) Uani 1 1 d . . . . .
C7A C 0.1133(3) 0.5327(3) 0.2120(2) 0.0241(8) Uani 1 1 d . . . . .
C8A C 0.1425(3) 0.5288(3) 0.2904(2) 0.0314(9) Uani 1 1 d . . . . .
H8A1 H 0.157473 0.462727 0.328380 0.038 Uiso 1 1 calc R U . . .
H8A2 H 0.148376 0.592062 0.308419 0.038 Uiso 1 1 calc R U . . .
C9A C 0.1028(3) 0.4367(3) 0.1806(2) 0.0235(8) Uani 1 1 d . . . . .
C10A C 0.1721(3) 0.3204(3) 0.2117(2) 0.0284(9) Uani 1 1 d . . . . .
H10A H 0.224049 0.302353 0.256363 0.034 Uiso 1 1 calc R U . . .
C11A C 0.1668(4) 0.2315(4) 0.1791(2) 0.0332(10) Uani 1 1 d . . . . .
H11A H 0.213892 0.152620 0.201710 0.040 Uiso 1 1 calc R U . . .
C12A C 0.0932(4) 0.2558(4) 0.1133(3) 0.0375(11) Uani 1 1 d . . . . .
H12A H 0.092823 0.193568 0.088649 0.045 Uiso 1 1 calc R U . . .
C13A C 0.0210(4) 0.3697(4) 0.0839(2) 0.0347(10) Uani 1 1 d . . . . .
H13A H -0.032594 0.386838 0.040611 0.042 Uiso 1 1 calc R U . . .
C14A C 0.0254(3) 0.4603(4) 0.1168(2) 0.0295(9) Uani 1 1 d . . . . .
H14A H -0.024746 0.539254 0.095582 0.035 Uiso 1 1 calc R U . . .
C15A C 0.3206(3) 0.4281(3) -0.0056(2) 0.0207(8) Uani 1 1 d . . . . .
C16A C 0.3247(3) 0.4785(3) -0.0841(2) 0.0238(8) Uani 1 1 d . . . . .
H16A H 0.342219 0.540658 -0.091265 0.029 Uiso 1 1 calc R U . . .
C17A C 0.3030(3) 0.4373(3) -0.1518(2) 0.0264(9) Uani 1 1 d . . . . .
H17A H 0.303926 0.472006 -0.206412 0.032 Uiso 1 1 calc R U . . .
C18A C 0.2797(3) 0.3452(3) -0.1407(2) 0.0255(9) Uani 1 1 d . . . . .
C19A C 0.2767(3) 0.2948(3) -0.0608(2) 0.0253(9) Uani 1 1 d . . . . .
H19A H 0.259884 0.232100 -0.053480 0.030 Uiso 1 1 calc R U . . .
C20A C 0.2978(3) 0.3356(3) 0.0072(2) 0.0238(8) Uani 1 1 d . . . . .
H20A H 0.296861 0.301264 0.061897 0.029 Uiso 1 1 calc R U . . .
C21A C 0.2586(4) 0.3476(4) -0.2864(3) 0.0523(13) Uani 1 1 d . . . . .
H21D H 0.194638 0.429342 -0.291886 0.078 Uiso 1 1 calc R U . . .
H21E H 0.247117 0.302720 -0.326063 0.078 Uiso 1 1 calc R U . . .
H21F H 0.333667 0.345322 -0.298368 0.078 Uiso 1 1 calc R U . . .
C22A C 0.3951(3) 0.8548(3) 0.0187(2) 0.0234(8) Uani 1 1 d . . . . .
C23A C 0.4110(3) 0.7846(3) 0.0925(2) 0.0255(9) Uani 1 1 d . . . . .
H23A H 0.410823 0.712535 0.092616 0.031 Uiso 1 1 calc R U . . .
C24A C 0.4271(3) 0.8203(3) 0.1660(2) 0.0282(9) Uani 1 1 d . . . . .
H24A H 0.437794 0.772091 0.216471 0.034 Uiso 1 1 calc R U . . .
C25A C 0.4280(3) 0.9248(3) 0.1675(2) 0.0281(9) Uani 1 1 d . . . . .
C26A C 0.4076(3) 0.9958(3) 0.0933(3) 0.0316(10) Uani 1 1 d . . . . .
H26A H 0.405340 1.068978 0.093171 0.038 Uiso 1 1 calc R U . . .
C27A C 0.3906(3) 0.9615(3) 0.0199(2) 0.0290(9) Uani 1 1 d . . . . .
H27A H 0.375800 1.011577 -0.030123 0.035 Uiso 1 1 calc R U . . .
C28A C 0.4545(4) 0.9593(4) 0.2456(3) 0.0415(11) Uani 1 1 d . . . . .
H28D H 0.383008 0.996530 0.279711 0.062 Uiso 1 1 calc R U . . .
H28E H 0.483183 1.014839 0.230896 0.062 Uiso 1 1 calc R U . . .
H28F H 0.514697 0.889232 0.277167 0.062 Uiso 1 1 calc R U . . .
S1A S 0.38698(8) 0.80809(8) -0.07837(6) 0.0247(2) Uani 1 1 d . . . . .
O2A O 0.2667(2) 0.8829(2) -0.10645(17) 0.0331(7) Uani 1 1 d . . . . .
O3A O 0.4152(2) 0.6860(2) -0.06224(16) 0.0293(6) Uani 1 1 d . . . . .
O4A O 0.4714(2) 0.8218(2) -0.13278(16) 0.0359(7) 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 C15 2.100(4) . ?
I1 C1 2.102(3) . ?
O1 C18 1.358(5) . ?
O1 C21 1.427(6) . ?
C1 C2 1.368(5) . ?
C1 C6 1.397(5) . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.484(5) . ?
C7 C8 1.314(5) . ?
C7 C9 1.476(5) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C14 1.383(5) . ?
C9 C10 1.389(6) . ?
C10 C11 1.385(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.372(5) . ?
C15 C20 1.375(5) . ?
C16 C17 1.378(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.374(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.373(6) . ?
C19 C20 1.384(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.375(5) . ?
C22 C27 1.382(5) . ?
C22 S1 1.776(4) . ?
C23 C24 1.387(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.379(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(6) . ?
C25 C28 1.513(6) . ?
C26 C27 1.374(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
S1 O3 1.431(3) . ?
S1 O2 1.453(3) . ?
S1 O4 1.458(3) . ?
I1A C15A 2.099(3) . ?
I1A C1A 2.116(3) . ?
O1A C18A 1.356(4) . ?
O1A C21A 1.422(5) . ?
C1A C2A 1.380(5) . ?
C1A C6A 1.382(5) . ?
C2A C3A 1.381(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.373(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.393(5) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.493(5) . ?
C7A C8A 1.331(5) . ?
C7A C9A 1.481(5) . ?
C8A H8A1 0.9500 . ?
C8A H8A2 0.9500 . ?
C9A C10A 1.390(5) . ?
C9A C14A 1.391(5) . ?
C10A C11A 1.367(5) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.381(6) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.365(6) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.384(5) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A C16A 1.377(5) . ?
C15A C20A 1.385(5) . ?
C16A C17A 1.373(5) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.384(5) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.393(5) . ?
C19A C20A 1.371(5) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C21A H21D 0.9800 . ?
C21A H21E 0.9800 . ?
C21A H21F 0.9800 . ?
C22A C27A 1.379(5) . ?
C22A C23A 1.385(5) . ?
C22A S1A 1.769(4) . ?
C23A C24A 1.384(5) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.385(5) . ?
C24A H24A 0.9500 . ?
C25A C26A 1.390(5) . ?
C25A C28A 1.498(5) . ?
C26A C27A 1.377(5) . ?
C26A H26A 0.9500 . ?
C27A H27A 0.9500 . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
S1A O4A 1.442(3) . ?
S1A O2A 1.455(3) . ?
S1A O3A 1.457(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
C15 I1 C1 92.81(14) . . ?
C18 O1 C21 117.4(4) . . ?
C2 C1 C6 123.0(3) . . ?
C2 C1 I1 116.8(3) . . ?
C6 C1 I1 120.2(3) . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 119.4(4) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.1(4) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 116.1(4) . . ?
C5 C6 C7 121.6(4) . . ?
C1 C6 C7 122.3(3) . . ?
C8 C7 C9 122.5(4) . . ?
C8 C7 C6 119.2(4) . . ?
C9 C7 C6 118.3(3) . . ?
C7 C8 H8A 120.0 . . ?
C7 C8 H8B 120.0 . . ?
H8A C8 H8B 120.0 . . ?
C14 C9 C10 117.5(4) . . ?
C14 C9 C7 122.2(4) . . ?
C10 C9 C7 120.3(4) . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.6(5) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.6(4) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C16 C15 C20 121.3(4) . . ?
C16 C15 I1 118.9(3) . . ?
C20 C15 I1 119.7(3) . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C18 C17 C16 119.8(4) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O1 C18 C19 115.1(4) . . ?
O1 C18 C17 124.5(4) . . ?
C19 C18 C17 120.4(4) . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 118.7(4) . . ?
C15 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
O1 C21 H21A 109.5 . . ?
O1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 120.2(4) . . ?
C23 C22 S1 120.5(3) . . ?
C27 C22 S1 119.3(3) . . ?
C22 C23 C24 119.8(4) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C25 C24 C23 120.6(4) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 118.6(4) . . ?
C24 C25 C28 120.8(5) . . ?
C26 C25 C28 120.5(5) . . ?
C27 C26 C25 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C22 119.2(4) . . ?
C26 C27 H27 120.4 . . ?
C22 C27 H27 120.4 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O3 S1 O2 113.79(18) . . ?
O3 S1 O4 113.94(19) . . ?
O2 S1 O4 110.49(16) . . ?
O3 S1 C22 107.50(18) . . ?
O2 S1 C22 105.65(16) . . ?
O4 S1 C22 104.64(17) . . ?
C15A I1A C1A 93.22(13) . . ?
C18A O1A C21A 117.6(3) . . ?
C2A C1A C6A 123.3(3) . . ?
C2A C1A I1A 115.5(3) . . ?
C6A C1A I1A 121.3(3) . . ?
C1A C2A C3A 118.2(4) . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A H2A 120.9 . . ?
C4A C3A C2A 120.8(4) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
C3A C4A C5A 119.7(4) . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A H4A 120.1 . . ?
C4A C5A C6A 121.4(4) . . ?
C4A C5A H5A 119.3 . . ?
C6A C5A H5A 119.3 . . ?
C1A C6A C5A 116.7(3) . . ?
C1A C6A C7A 123.1(3) . . ?
C5A C6A C7A 120.2(3) . . ?
C8A C7A C9A 122.3(4) . . ?
C8A C7A C6A 120.2(3) . . ?
C9A C7A C6A 117.5(3) . . ?
C7A C8A H8A1 120.0 . . ?
C7A C8A H8A2 120.0 . . ?
H8A1 C8A H8A2 120.0 . . ?
C10A C9A C14A 118.0(4) . . ?
C10A C9A C7A 121.4(3) . . ?
C14A C9A C7A 120.6(3) . . ?
C11A C10A C9A 121.0(4) . . ?
C11A C10A H10A 119.5 . . ?
C9A C10A H10A 119.5 . . ?
C10A C11A C12A 120.3(4) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A H11A 119.9 . . ?
C13A C12A C11A 119.7(4) . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C12A C13A C14A 120.4(4) . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A H13A 119.8 . . ?
C13A C14A C9A 120.5(4) . . ?
C13A C14A H14A 119.7 . . ?
C9A C14A H14A 119.7 . . ?
C16A C15A C20A 122.2(3) . . ?
C16A C15A I1A 119.6(3) . . ?
C20A C15A I1A 118.2(3) . . ?
C17A C16A C15A 118.8(3) . . ?
C17A C16A H16A 120.6 . . ?
C15A C16A H16A 120.6 . . ?
C16A C17A C18A 120.1(3) . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
O1A C18A C17A 124.2(3) . . ?
O1A C18A C19A 115.5(3) . . ?
C17A C18A C19A 120.3(3) . . ?
C20A C19A C18A 120.0(3) . . ?
C20A C19A H19A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C19A C20A C15A 118.5(3) . . ?
C19A C20A H20A 120.7 . . ?
C15A C20A H20A 120.7 . . ?
O1A C21A H21D 109.5 . . ?
O1A C21A H21E 109.5 . . ?
H21D C21A H21E 109.5 . . ?
O1A C21A H21F 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C27A C22A C23A 119.7(4) . . ?
C27A C22A S1A 118.7(3) . . ?
C23A C22A S1A 121.5(3) . . ?
C24A C23A C22A 119.4(3) . . ?
C24A C23A H23A 120.3 . . ?
C22A C23A H23A 120.3 . . ?
C23A C24A C25A 121.5(4) . . ?
C23A C24A H24A 119.2 . . ?
C25A C24A H24A 119.2 . . ?
C24A C25A C26A 118.0(4) . . ?
C24A C25A C28A 121.7(4) . . ?
C26A C25A C28A 120.3(4) . . ?
C27A C26A C25A 121.0(4) . . ?
C27A C26A H26A 119.5 . . ?
C25A C26A H26A 119.5 . . ?
C26A C27A C22A 120.3(4) . . ?
C26A C27A H27A 119.9 . . ?
C22A C27A H27A 119.9 . . ?
C25A C28A H28D 109.5 . . ?
C25A C28A H28E 109.5 . . ?
H28D C28A H28E 109.5 . . ?
C25A C28A H28F 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
O4A S1A O2A 113.08(17) . . ?
O4A S1A O3A 112.71(16) . . ?
O2A S1A O3A 111.39(15) . . ?
O4A S1A C22A 106.36(16) . . ?
O2A S1A C22A 106.35(16) . . ?
O3A S1A C22A 106.36(17) . . ?

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 -1.5(6) . . . . ?
I1 C1 C2 C3 177.5(3) . . . . ?
C1 C2 C3 C4 -0.3(6) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 177.6(4) . . . . ?
C2 C1 C6 C5 2.3(5) . . . . ?
I1 C1 C6 C5 -176.7(3) . . . . ?
C2 C1 C6 C7 -176.7(4) . . . . ?
I1 C1 C6 C7 4.3(5) . . . . ?
C5 C6 C7 C8 -98.4(5) . . . . ?
C1 C6 C7 C8 80.5(5) . . . . ?
C5 C6 C7 C9 84.3(5) . . . . ?
C1 C6 C7 C9 -96.8(4) . . . . ?
C8 C7 C9 C14 147.0(4) . . . . ?
C6 C7 C9 C14 -35.9(6) . . . . ?
C8 C7 C9 C10 -36.4(6) . . . . ?
C6 C7 C9 C10 140.8(4) . . . . ?
C14 C9 C10 C11 -2.3(6) . . . . ?
C7 C9 C10 C11 -179.1(4) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C13 0.5(8) . . . . ?
C11 C12 C13 C14 2.1(8) . . . . ?
C12 C13 C14 C9 -4.9(7) . . . . ?
C10 C9 C14 C13 4.9(6) . . . . ?
C7 C9 C14 C13 -178.4(4) . . . . ?
C20 C15 C16 C17 2.0(6) . . . . ?
I1 C15 C16 C17 -174.5(3) . . . . ?
C15 C16 C17 C18 -0.3(6) . . . . ?
C21 O1 C18 C19 160.7(4) . . . . ?
C21 O1 C18 C17 -17.9(6) . . . . ?
C16 C17 C18 O1 177.4(4) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
O1 C18 C19 C20 -177.7(4) . . . . ?
C17 C18 C19 C20 1.0(6) . . . . ?
C16 C15 C20 C19 -2.2(6) . . . . ?
I1 C15 C20 C19 174.3(3) . . . . ?
C18 C19 C20 C15 0.7(6) . . . . ?
C27 C22 C23 C24 -0.3(6) . . . . ?
S1 C22 C23 C24 179.2(3) . . . . ?
C22 C23 C24 C25 -0.7(7) . . . . ?
C23 C24 C25 C26 1.4(7) . . . . ?
C23 C24 C25 C28 176.3(4) . . . . ?
C24 C25 C26 C27 -1.1(7) . . . . ?
C28 C25 C26 C27 -176.0(4) . . . . ?
C25 C26 C27 C22 0.1(6) . . . . ?
C23 C22 C27 C26 0.6(6) . . . . ?
S1 C22 C27 C26 -178.9(3) . . . . ?
C23 C22 S1 O3 16.7(4) . . . . ?
C27 C22 S1 O3 -163.9(3) . . . . ?
C23 C22 S1 O2 -105.2(3) . . . . ?
C27 C22 S1 O2 74.3(3) . . . . ?
C23 C22 S1 O4 138.2(3) . . . . ?
C27 C22 S1 O4 -42.4(3) . . . . ?
C6A C1A C2A C3A -0.5(5) . . . . ?
I1A C1A C2A C3A 178.8(3) . . . . ?
C1A C2A C3A C4A 0.5(5) . . . . ?
C2A C3A C4A C5A -0.5(6) . . . . ?
C3A C4A C5A C6A 0.4(6) . . . . ?
C2A C1A C6A C5A 0.4(5) . . . . ?
I1A C1A C6A C5A -178.9(2) . . . . ?
C2A C1A C6A C7A -180.0(3) . . . . ?
I1A C1A C6A C7A 0.8(5) . . . . ?
C4A C5A C6A C1A -0.3(5) . . . . ?
C4A C5A C6A C7A 180.0(3) . . . . ?
C1A C6A C7A C8A 93.2(5) . . . . ?
C5A C6A C7A C8A -87.2(4) . . . . ?
C1A C6A C7A C9A -85.5(4) . . . . ?
C5A C6A C7A C9A 94.2(4) . . . . ?
C8A C7A C9A C10A -31.6(5) . . . . ?
C6A C7A C9A C10A 147.0(3) . . . . ?
C8A C7A C9A C14A 150.6(4) . . . . ?
C6A C7A C9A C14A -30.8(5) . . . . ?
C14A C9A C10A C11A 1.7(6) . . . . ?
C7A C9A C10A C11A -176.2(3) . . . . ?
C9A C10A C11A C12A 1.0(6) . . . . ?
C10A C11A C12A C13A -3.5(6) . . . . ?
C11A C12A C13A C14A 3.3(6) . . . . ?
C12A C13A C14A C9A -0.5(6) . . . . ?
C10A C9A C14A C13A -2.0(5) . . . . ?
C7A C9A C14A C13A 175.9(3) . . . . ?
C20A C15A C16A C17A 1.4(5) . . . . ?
I1A C15A C16A C17A -179.0(3) . . . . ?
C15A C16A C17A C18A -1.2(5) . . . . ?
C21A O1A C18A C17A -1.6(5) . . . . ?
C21A O1A C18A C19A 178.6(4) . . . . ?
C16A C17A C18A O1A -179.0(3) . . . . ?
C16A C17A C18A C19A 0.9(6) . . . . ?
O1A C18A C19A C20A 179.2(3) . . . . ?
C17A C18A C19A C20A -0.6(5) . . . . ?
C18A C19A C20A C15A 0.8(5) . . . . ?
C16A C15A C20A C19A -1.2(5) . . . . ?
I1A C15A C20A C19A 179.3(3) . . . . ?
C27A C22A C23A C24A -2.7(5) . . . . ?
S1A C22A C23A C24A 174.4(3) . . . . ?
C22A C23A C24A C25A -0.2(5) . . . . ?
C23A C24A C25A C26A 2.4(6) . . . . ?
C23A C24A C25A C28A -175.2(3) . . . . ?
C24A C25A C26A C27A -2.0(6) . . . . ?
C28A C25A C26A C27A 175.8(4) . . . . ?
C25A C26A C27A C22A -0.8(6) . . . . ?
C23A C22A C27A C26A 3.2(6) . . . . ?
S1A C22A C27A C26A -174.0(3) . . . . ?
C27A C22A S1A O4A 49.4(3) . . . . ?
C23A C22A S1A O4A -127.6(3) . . . . ?
C27A C22A S1A O2A -71.4(3) . . . . ?
C23A C22A S1A O2A 111.6(3) . . . . ?
C27A C22A S1A O3A 169.8(3) . . . . ?
C23A C22A S1A O3A -7.3(3) . . . . ?

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
_geom_hbond_publ_flag
C17A H17A O4 0.95 2.51 3.087(4) 119.6 2_665 yes
C16A H16A O3A 0.95 2.62 3.537(4) 161.6 . yes
C16A H16A O4 0.95 2.65 3.156(4) 114.0 2_665 yes
C2A H2A O3A 0.95 2.54 3.471(5) 167.2 . yes
C27 H27 I1A 0.95 3.18 3.895(4) 133.2 . yes

_refine_diff_density_max         1.179
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.102

