# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_140111e

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H22 F4 I O3 S'
_chemical_formula_weight         581.37

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           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                   9.8987(8)
_cell_length_b                   24.374(2)
_cell_length_c                   10.0794(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.820(2)
_cell_angle_gamma                90.00
_cell_volume                     2339.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3546
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      23.16

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1156
_exptl_absorpt_coefficient_mu    1.512
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7321
_exptl_absorpt_correction_T_max  0.7725
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13544
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.50
_reflns_number_total             4341
_reflns_number_gt                3405
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0805P)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         4341
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1419
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3026(6) 0.06955(18) 0.8802(5) 0.0656(14) Uani 1 1 d . . .
C1 C 0.6362(7) 0.1152(2) 0.6650(6) 0.0490(15) Uani 1 1 d . . .
C2 C 0.7058(6) 0.1336(2) 0.5718(7) 0.0533(16) Uani 1 1 d . . .
H2 H 0.7900 0.1524 0.6045 0.064 Uiso 1 1 calc R . .
C3 C 0.6542(5) 0.1249(2) 0.4321(6) 0.0368(12) Uani 1 1 d . . .
C4 C 0.5286(5) 0.0968(2) 0.3865(6) 0.0349(12) Uani 1 1 d . . .
C5 C 0.4560(6) 0.0757(2) 0.4748(6) 0.0375(12) Uani 1 1 d . . .
C6 C 0.5089(7) 0.0871(2) 0.6182(6) 0.0460(15) Uani 1 1 d . . .
H6 H 0.4595 0.0760 0.6799 0.055 Uiso 1 1 calc R . .
C7 C 0.2621(5) 0.1271(2) 0.1450(5) 0.0361(12) Uani 1 1 d . . .
C8 C 0.2661(6) 0.1846(2) 0.1484(6) 0.0419(13) Uani 1 1 d . . .
C9 C 0.1403(6) 0.2116(2) 0.1369(7) 0.0494(15) Uani 1 1 d . . .
H9 H 0.1372 0.2497 0.1361 0.059 Uiso 1 1 calc R . .
C10 C 0.0189(6) 0.1814(3) 0.1265(7) 0.0520(16) Uani 1 1 d . . .
C11 C 0.0135(6) 0.1253(2) 0.1185(6) 0.0456(14) Uani 1 1 d . . .
H11 H -0.0707 0.1064 0.1055 0.055 Uiso 1 1 calc R . .
C12 C 0.1373(6) 0.0983(2) 0.1305(6) 0.0428(13) Uani 1 1 d . . .
H12 H 0.1382 0.0601 0.1289 0.051 Uiso 1 1 calc R . .
C13 C 0.7364(8) 0.3215(3) 0.1208(12) 0.106(4) Uani 1 1 d . . .
H13A H 0.8164 0.2994 0.1202 0.159 Uiso 1 1 calc R . .
H13B H 0.7599 0.3457 0.1990 0.159 Uiso 1 1 calc R . .
H13C H 0.7092 0.3428 0.0377 0.159 Uiso 1 1 calc R . .
C14 C 0.3908(6) 0.2173(2) 0.1483(6) 0.0387(12) Uani 1 1 d . . .
C15 C 0.4525(6) 0.2532(2) 0.2526(7) 0.0495(15) Uani 1 1 d . . .
H15 H 0.4197 0.2554 0.3305 0.059 Uiso 1 1 calc R . .
C16 C 0.5641(7) 0.2863(3) 0.2419(8) 0.0606(18) Uani 1 1 d . . .
H16 H 0.6043 0.3101 0.3140 0.073 Uiso 1 1 calc R . .
C17 C 0.6170(6) 0.2852(3) 0.1295(8) 0.0584(18) Uani 1 1 d . . .
C18 C 0.5565(7) 0.2485(3) 0.0272(7) 0.0573(17) Uani 1 1 d . . .
H18 H 0.5904 0.2461 -0.0500 0.069 Uiso 1 1 calc R . .
C19 C 0.4453(7) 0.2149(3) 0.0362(7) 0.0523(15) Uani 1 1 d . . .
H19 H 0.4070 0.1905 -0.0349 0.063 Uiso 1 1 calc R . .
C21 C 0.0696(7) 0.0300(3) 0.7314(8) 0.0619(18) Uani 1 1 d . . .
C22 C 0.7369(6) 0.1458(3) 0.3363(7) 0.0537(16) Uani 1 1 d . . .
H22A H 0.7797 0.1154 0.3026 0.080 Uiso 1 1 calc R . .
H22B H 0.8086 0.1706 0.3855 0.080 Uiso 1 1 calc R . .
H22C H 0.6750 0.1647 0.2600 0.080 Uiso 1 1 calc R . .
C23 C 0.6930(8) 0.1254(3) 0.8169(7) 0.071(2) Uani 1 1 d . . .
H23A H 0.7348 0.0924 0.8617 0.107 Uiso 1 1 calc R . .
H23B H 0.6179 0.1366 0.8544 0.107 Uiso 1 1 calc R . .
H23C H 0.7625 0.1539 0.8318 0.107 Uiso 1 1 calc R . .
C24 C 0.3196(6) 0.0431(3) 0.4328(7) 0.0535(16) Uani 1 1 d . . .
H24A H 0.2414 0.0679 0.4109 0.080 Uiso 1 1 calc R . .
H24B H 0.3133 0.0197 0.5076 0.080 Uiso 1 1 calc R . .
H24C H 0.3182 0.0210 0.3535 0.080 Uiso 1 1 calc R . .
F1 F -0.1015(4) 0.20869(18) 0.1145(6) 0.0883(15) Uani 1 1 d . . .
F2 F 0.0066(6) -0.0156(2) 0.6819(6) 0.117(2) Uani 1 1 d . . .
F3 F 0.0720(5) 0.0605(2) 0.6257(5) 0.0839(13) Uani 1 1 d . . .
F4 F -0.0073(6) 0.0542(4) 0.7991(7) 0.147(3) Uani 1 1 d . . .
I1 I 0.44677(3) 0.080765(13) 0.17435(3) 0.03628(16) Uani 1 1 d . . .
O2 O 0.2225(6) -0.0155(2) 0.9503(5) 0.0728(14) Uani 1 1 d . . .
O3 O 0.3103(5) -0.01180(19) 0.7496(5) 0.0687(14) Uani 1 1 d . . .
S3 S 0.24551(15) 0.01636(6) 0.84096(15) 0.0418(3) 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
O1 S3 1.427(4) . ?
C1 C2 1.383(9) . ?
C1 C6 1.398(9) . ?
C1 C23 1.501(8) . ?
C2 C3 1.377(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(7) . ?
C3 C22 1.515(8) . ?
C4 C5 1.387(8) . ?
C4 I1 2.107(5) . ?
C5 C6 1.424(8) . ?
C5 C24 1.524(8) . ?
C6 H6 0.9300 . ?
C7 C12 1.393(8) . ?
C7 C8 1.403(8) . ?
C7 I1 2.099(5) . ?
C8 C9 1.384(8) . ?
C8 C14 1.469(8) . ?
C9 C10 1.389(8) . ?
C9 H9 0.9300 . ?
C10 F1 1.342(7) . ?
C10 C11 1.369(9) . ?
C11 C12 1.367(8) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C17 1.499(9) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.377(8) . ?
C14 C19 1.380(8) . ?
C15 C16 1.395(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.372(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(10) . ?
C18 C19 1.395(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C21 F4 1.294(9) . ?
C21 F3 1.304(8) . ?
C21 F2 1.306(9) . ?
C21 S3 1.820(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O2 S3 1.416(5) . ?
O3 S3 1.433(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
C2 C1 C6 120.0(5) . . ?
C2 C1 C23 121.4(6) . . ?
C6 C1 C23 118.6(6) . . ?
C3 C2 C1 122.0(5) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 117.7(5) . . ?
C2 C3 C22 119.1(5) . . ?
C4 C3 C22 123.2(5) . . ?
C3 C4 C5 123.2(5) . . ?
C3 C4 I1 119.4(4) . . ?
C5 C4 I1 117.4(4) . . ?
C4 C5 C6 117.8(5) . . ?
C4 C5 C24 126.2(5) . . ?
C6 C5 C24 115.9(5) . . ?
C1 C6 C5 119.1(6) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C12 C7 C8 121.6(5) . . ?
C12 C7 I1 117.2(4) . . ?
C8 C7 I1 121.1(4) . . ?
C9 C8 C7 117.0(5) . . ?
C9 C8 C14 118.6(5) . . ?
C7 C8 C14 124.0(5) . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
F1 C10 C11 118.1(6) . . ?
F1 C10 C9 118.2(5) . . ?
C11 C10 C9 123.6(5) . . ?
C12 C11 C10 117.1(5) . . ?
C12 C11 H11 121.4 . . ?
C10 C11 H11 121.4 . . ?
C11 C12 C7 121.0(5) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C17 C13 H13A 109.5 . . ?
C17 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C17 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 117.4(5) . . ?
C15 C14 C8 122.9(5) . . ?
C19 C14 C8 119.6(5) . . ?
C14 C15 C16 120.3(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 122.8(6) . . ?
C17 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C16 C17 C18 116.5(6) . . ?
C16 C17 C13 121.4(8) . . ?
C18 C17 C13 122.1(8) . . ?
C17 C18 C19 121.6(6) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C14 C19 C18 121.4(6) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
F4 C21 F3 108.4(7) . . ?
F4 C21 F2 107.5(7) . . ?
F3 C21 F2 106.6(6) . . ?
F4 C21 S3 111.5(5) . . ?
F3 C21 S3 111.8(5) . . ?
F2 C21 S3 110.7(5) . . ?
C3 C22 H22A 109.5 . . ?
C3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 C23 H23A 109.5 . . ?
C1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C24 H24A 109.5 . . ?
C5 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C5 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C7 I1 C4 97.0(2) . . ?
O2 S3 O1 114.7(3) . . ?
O2 S3 O3 115.7(3) . . ?
O1 S3 O3 113.6(3) . . ?
O2 S3 C21 104.0(3) . . ?
O1 S3 C21 104.1(3) . . ?
O3 S3 C21 102.7(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
C6 C1 C2 C3 -0.4(9) . . . . ?
C23 C1 C2 C3 -179.4(6) . . . . ?
C1 C2 C3 C4 0.0(9) . . . . ?
C1 C2 C3 C22 -179.4(6) . . . . ?
C2 C3 C4 C5 -2.2(8) . . . . ?
C22 C3 C4 C5 177.2(5) . . . . ?
C2 C3 C4 I1 -178.6(4) . . . . ?
C22 C3 C4 I1 0.7(7) . . . . ?
C3 C4 C5 C6 4.6(8) . . . . ?
I1 C4 C5 C6 -178.9(4) . . . . ?
C3 C4 C5 C24 -178.3(5) . . . . ?
I1 C4 C5 C24 -1.8(7) . . . . ?
C2 C1 C6 C5 2.9(8) . . . . ?
C23 C1 C6 C5 -178.2(6) . . . . ?
C4 C5 C6 C1 -4.8(8) . . . . ?
C24 C5 C6 C1 177.8(5) . . . . ?
C12 C7 C8 C9 0.1(9) . . . . ?
I1 C7 C8 C9 -176.0(4) . . . . ?
C12 C7 C8 C14 -173.1(5) . . . . ?
I1 C7 C8 C14 10.9(8) . . . . ?
C7 C8 C9 C10 1.7(9) . . . . ?
C14 C8 C9 C10 175.3(6) . . . . ?
C8 C9 C10 F1 -179.5(6) . . . . ?
C8 C9 C10 C11 -4.1(11) . . . . ?
F1 C10 C11 C12 179.7(6) . . . . ?
C9 C10 C11 C12 4.3(10) . . . . ?
C10 C11 C12 C7 -2.3(9) . . . . ?
C8 C7 C12 C11 0.2(9) . . . . ?
I1 C7 C12 C11 176.4(4) . . . . ?
C9 C8 C14 C15 66.3(8) . . . . ?
C7 C8 C14 C15 -120.6(7) . . . . ?
C9 C8 C14 C19 -109.7(7) . . . . ?
C7 C8 C14 C19 63.4(8) . . . . ?
C19 C14 C15 C16 1.1(9) . . . . ?
C8 C14 C15 C16 -175.0(5) . . . . ?
C14 C15 C16 C17 0.3(10) . . . . ?
C15 C16 C17 C18 -1.4(10) . . . . ?
C15 C16 C17 C13 179.5(6) . . . . ?
C16 C17 C18 C19 1.1(10) . . . . ?
C13 C17 C18 C19 -179.9(7) . . . . ?
C15 C14 C19 C18 -1.4(9) . . . . ?
C8 C14 C19 C18 174.8(6) . . . . ?
C17 C18 C19 C14 0.3(10) . . . . ?
C12 C7 I1 C4 -105.0(4) . . . . ?
C8 C7 I1 C4 71.2(5) . . . . ?
C3 C4 I1 C7 -116.7(4) . . . . ?
C5 C4 I1 C7 66.6(4) . . . . ?
F4 C21 S3 O2 56.9(7) . . . . ?
F3 C21 S3 O2 178.5(5) . . . . ?
F2 C21 S3 O2 -62.7(6) . . . . ?
F4 C21 S3 O1 -63.5(7) . . . . ?
F3 C21 S3 O1 58.1(6) . . . . ?
F2 C21 S3 O1 176.9(6) . . . . ?
F4 C21 S3 O3 177.8(7) . . . . ?
F3 C21 S3 O3 -60.6(6) . . . . ?
F2 C21 S3 O3 58.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.747
_refine_diff_density_min         -1.241
_refine_diff_density_rms         0.173
_database_code_depnum_ccdc_archive 'CCDC 981367'
