# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sb535_hy_1-OC(CF3)3
_database_code_depnum_ccdc_archive 'CCDC 981372'
_audit_update_record             
;
2014-01-14 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1,3-Bis((perfluoro-tert.butoxy)methyl)-5-iodobenzene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H7 F18 I O2'

_chemical_formula_sum            'C16 H7 F18 I O2'
_chemical_formula_weight         700.12

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'
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                   7.2087(4)
_cell_length_b                   11.5510(9)
_cell_length_c                   14.1610(8)
_cell_angle_alpha                68.222(5)
_cell_angle_beta                 76.825(5)
_cell_angle_gamma                73.919(7)
_cell_volume                     1041.75(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    118
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       rods
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    2.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    1.711
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7158
_exptl_absorpt_correction_T_max  0.8879
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 dx = 40 mm, 20 sec./deg., 2 deg., 6 sets, 273 frames,
 5496 refl. postref. 
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13325
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.48
_reflns_number_total             4754
_reflns_number_gt                4448
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'


_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)+(0.0256P)²+0.9814P] 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         4754
_refine_ls_number_parameters     334
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0247
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0612
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.2595(3) 0.4328(2) 0.42701(15) 0.0160(4) Uani 1 1 d . . .
C11 C 0.2633(3) 0.3681(2) 0.35178(17) 0.0206(4) Uani 1 1 d . . .
H11A H 0.1910 0.2984 0.3841 0.025 Uiso 1 1 calc R . .
H11B H 0.2032 0.4299 0.2910 0.025 Uiso 1 1 calc R . .
O11 O 0.4687(2) 0.31741(14) 0.32197(11) 0.0184(3) Uani 1 1 d . . .
C12 C 0.5233(3) 0.2311(2) 0.26793(15) 0.0169(4) Uani 1 1 d . . .
C13 C 0.4901(4) 0.2968(2) 0.15408(17) 0.0255(5) Uani 1 1 d . . .
F11 F 0.3118(2) 0.36576(17) 0.14607(12) 0.0434(4) Uani 1 1 d . . .
F12 F 0.6142(3) 0.37380(16) 0.10357(12) 0.0435(4) Uani 1 1 d . . .
F13 F 0.5191(2) 0.21287(15) 0.10632(11) 0.0338(3) Uani 1 1 d . . .
C14 C 0.7447(3) 0.1816(2) 0.27426(18) 0.0239(5) Uani 1 1 d . . .
F14 F 0.8318(2) 0.27666(16) 0.25542(14) 0.0383(4) Uani 1 1 d . . .
F15 F 0.7735(2) 0.10277(16) 0.36828(11) 0.0382(4) Uani 1 1 d . . .
F16 F 0.8335(2) 0.11892(14) 0.20885(11) 0.0303(3) Uani 1 1 d . . .
C15 C 0.4201(4) 0.1162(2) 0.31852(19) 0.0283(5) Uani 1 1 d . . .
F17 F 0.2445(2) 0.14565(17) 0.29019(14) 0.0413(4) Uani 1 1 d . . .
F18 F 0.5218(3) 0.01497(14) 0.29277(14) 0.0445(4) Uani 1 1 d . . .
F19 F 0.3944(3) 0.08453(15) 0.41995(12) 0.0415(4) Uani 1 1 d . . .
C2 C 0.3119(3) 0.3613(2) 0.52413(16) 0.0172(4) Uani 1 1 d . . .
H2 H 0.3524 0.2712 0.5427 0.021 Uiso 1 1 calc R . .
C3 C 0.3051(3) 0.4215(2) 0.59403(15) 0.0162(4) Uani 1 1 d . . .
C31 C 0.3576(3) 0.3441(2) 0.69985(16) 0.0210(4) Uani 1 1 d . . .
H31A H 0.4674 0.2711 0.6973 0.025 Uiso 1 1 calc R . .
H31B H 0.3955 0.3974 0.7302 0.025 Uiso 1 1 calc R . .
O31 O 0.1825(2) 0.29945(15) 0.76004(11) 0.0195(3) Uani 1 1 d . . .
C32 C 0.1568(3) 0.25953(19) 0.86669(15) 0.0164(4) Uani 1 1 d . . .
C33 C 0.1506(4) 0.3689(2) 0.90773(17) 0.0245(5) Uani 1 1 d . . .
F31 F 0.0502(3) 0.35280(16) 1.00072(11) 0.0415(4) Uani 1 1 d . . .
F32 F 0.0698(2) 0.48044(14) 0.84437(13) 0.0383(4) Uani 1 1 d . . .
F33 F 0.3285(2) 0.37688(15) 0.91210(11) 0.0340(3) Uani 1 1 d . . .
C34 C 0.3117(3) 0.1410(2) 0.91448(17) 0.0236(4) Uani 1 1 d . . .
F34 F 0.2938(3) 0.04056(14) 0.89638(14) 0.0419(4) Uani 1 1 d . . .
F35 F 0.4914(2) 0.15898(15) 0.87620(12) 0.0357(4) Uani 1 1 d . . .
F36 F 0.2929(2) 0.11233(15) 1.01577(11) 0.0357(3) Uani 1 1 d . . .
C35 C -0.0468(3) 0.2243(2) 0.89592(17) 0.0255(5) Uani 1 1 d . . .
F37 F -0.0619(2) 0.15511(17) 0.84361(12) 0.0402(4) Uani 1 1 d . . .
F38 F -0.1866(2) 0.33050(17) 0.87447(12) 0.0392(4) Uani 1 1 d . . .
F39 F -0.0829(2) 0.16018(15) 0.99543(10) 0.0337(3) Uani 1 1 d . . .
C4 C 0.2484(3) 0.5535(2) 0.56659(15) 0.0167(4) Uani 1 1 d . . .
H4 H 0.2453 0.5952 0.6137 0.020 Uiso 1 1 calc R . .
C5 C 0.1962(3) 0.6237(2) 0.46951(15) 0.0163(4) Uani 1 1 d . . .
I5 I 0.11076(2) 0.822494(13) 0.426153(11) 0.02465(6) Uani 1 1 d . . .
C6 C 0.2007(3) 0.5644(2) 0.39979(15) 0.0159(4) Uani 1 1 d . . .
H6 H 0.1638 0.6136 0.3338 0.019 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.387(3) . ?
C1 C2 1.392(3) . ?
C1 C11 1.503(3) . ?
C11 O11 1.460(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O11 C12 1.395(2) . ?
C12 C13 1.549(3) . ?
C12 C14 1.550(3) . ?
C12 C15 1.559(3) . ?
C13 F11 1.316(3) . ?
C13 F13 1.323(3) . ?
C13 F12 1.335(3) . ?
C14 F14 1.326(3) . ?
C14 F16 1.328(2) . ?
C14 F15 1.329(3) . ?
C15 F18 1.325(3) . ?
C15 F19 1.326(3) . ?
C15 F17 1.330(3) . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 C31 1.505(3) . ?
C31 O31 1.460(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
O31 C32 1.389(2) . ?
C32 C34 1.546(3) . ?
C32 C35 1.556(3) . ?
C32 C33 1.561(3) . ?
C33 F31 1.323(3) . ?
C33 F33 1.328(3) . ?
C33 F32 1.330(3) . ?
C34 F34 1.321(3) . ?
C34 F35 1.327(3) . ?
C34 F36 1.330(3) . ?
C35 F37 1.313(3) . ?
C35 F39 1.329(2) . ?
C35 F38 1.338(3) . ?
C4 C5 1.389(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(3) . ?
C5 I5 2.091(2) . ?
C6 H6 0.9500 . ?

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
C6 C1 C2 119.87(19) . . ?
C6 C1 C11 119.65(18) . . ?
C2 C1 C11 120.47(19) . . ?
O11 C11 C1 105.95(15) . . ?
O11 C11 H11A 110.5 . . ?
C1 C11 H11A 110.5 . . ?
O11 C11 H11B 110.5 . . ?
C1 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C12 O11 C11 120.83(15) . . ?
O11 C12 C13 112.03(17) . . ?
O11 C12 C14 102.99(16) . . ?
C13 C12 C14 109.75(18) . . ?
O11 C12 C15 112.99(17) . . ?
C13 C12 C15 109.88(18) . . ?
C14 C12 C15 108.95(18) . . ?
F11 C13 F13 108.08(19) . . ?
F11 C13 F12 107.9(2) . . ?
F13 C13 F12 107.06(19) . . ?
F11 C13 C12 111.35(18) . . ?
F13 C13 C12 111.87(19) . . ?
F12 C13 C12 110.35(19) . . ?
F14 C14 F16 108.35(19) . . ?
F14 C14 F15 106.79(19) . . ?
F16 C14 F15 107.75(18) . . ?
F14 C14 C12 111.25(18) . . ?
F16 C14 C12 112.26(18) . . ?
F15 C14 C12 110.22(18) . . ?
F18 C15 F19 108.7(2) . . ?
F18 C15 F17 107.7(2) . . ?
F19 C15 F17 107.1(2) . . ?
F18 C15 C12 111.78(19) . . ?
F19 C15 C12 110.30(19) . . ?
F17 C15 C12 111.1(2) . . ?
C3 C2 C1 120.23(19) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.04(19) . . ?
C4 C3 C31 119.67(19) . . ?
C2 C3 C31 120.29(19) . . ?
O31 C31 C3 105.64(15) . . ?
O31 C31 H31A 110.6 . . ?
C3 C31 H31A 110.6 . . ?
O31 C31 H31B 110.6 . . ?
C3 C31 H31B 110.6 . . ?
H31A C31 H31B 108.7 . . ?
C32 O31 C31 120.88(15) . . ?
O31 C32 C34 113.23(17) . . ?
O31 C32 C35 102.58(16) . . ?
C34 C32 C35 109.53(18) . . ?
O31 C32 C33 112.01(17) . . ?
C34 C32 C33 109.78(17) . . ?
C35 C32 C33 109.44(18) . . ?
F31 C33 F33 107.65(19) . . ?
F31 C33 F32 108.7(2) . . ?
F33 C33 F32 106.90(19) . . ?
F31 C33 C32 112.17(19) . . ?
F33 C33 C32 111.50(19) . . ?
F32 C33 C32 109.75(18) . . ?
F34 C34 F35 107.9(2) . . ?
F34 C34 F36 107.59(19) . . ?
F35 C34 F36 107.52(19) . . ?
F34 C34 C32 110.47(19) . . ?
F35 C34 C32 111.65(18) . . ?
F36 C34 C32 111.49(18) . . ?
F37 C35 F39 108.3(2) . . ?
F37 C35 F38 107.5(2) . . ?
F39 C35 F38 107.57(19) . . ?
F37 C35 C32 111.32(18) . . ?
F39 C35 C32 111.99(18) . . ?
F38 C35 C32 109.94(19) . . ?
C5 C4 C3 119.19(18) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 121.12(19) . . ?
C6 C5 I5 118.91(15) . . ?
C4 C5 I5 119.97(15) . . ?
C5 C6 C1 119.55(18) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C11 O11 111.9(2) . . . . ?
C2 C1 C11 O11 -69.0(2) . . . . ?
C1 C11 O11 C12 167.78(17) . . . . ?
C11 O11 C12 C13 74.1(2) . . . . ?
C11 O11 C12 C14 -168.02(18) . . . . ?
C11 O11 C12 C15 -50.6(2) . . . . ?
O11 C12 C13 F11 -51.2(3) . . . . ?
C14 C12 C13 F11 -164.9(2) . . . . ?
C15 C12 C13 F11 75.3(2) . . . . ?
O11 C12 C13 F13 -172.24(18) . . . . ?
C14 C12 C13 F13 74.0(2) . . . . ?
C15 C12 C13 F13 -45.8(3) . . . . ?
O11 C12 C13 F12 68.7(2) . . . . ?
C14 C12 C13 F12 -45.1(2) . . . . ?
C15 C12 C13 F12 -164.86(18) . . . . ?
O11 C12 C14 F14 -44.7(2) . . . . ?
C13 C12 C14 F14 74.7(2) . . . . ?
C15 C12 C14 F14 -164.92(18) . . . . ?
O11 C12 C14 F16 -166.34(18) . . . . ?
C13 C12 C14 F16 -46.9(3) . . . . ?
C15 C12 C14 F16 73.5(2) . . . . ?
O11 C12 C14 F15 73.5(2) . . . . ?
C13 C12 C14 F15 -167.00(18) . . . . ?
C15 C12 C14 F15 -46.7(2) . . . . ?
O11 C12 C15 F18 -155.77(19) . . . . ?
C13 C12 C15 F18 78.3(2) . . . . ?
C14 C12 C15 F18 -42.0(3) . . . . ?
O11 C12 C15 F19 -34.7(3) . . . . ?
C13 C12 C15 F19 -160.59(19) . . . . ?
C14 C12 C15 F19 79.1(2) . . . . ?
O11 C12 C15 F17 83.9(2) . . . . ?
C13 C12 C15 F17 -42.0(2) . . . . ?
C14 C12 C15 F17 -162.28(18) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C11 C1 C2 C3 -178.96(18) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C2 C3 C31 178.70(17) . . . . ?
C4 C3 C31 O31 97.4(2) . . . . ?
C2 C3 C31 O31 -82.2(2) . . . . ?
C3 C31 O31 C32 -159.94(18) . . . . ?
C31 O31 C32 C34 -63.1(2) . . . . ?
C31 O31 C32 C35 178.92(18) . . . . ?
C31 O31 C32 C33 61.7(2) . . . . ?
O31 C32 C33 F31 153.79(19) . . . . ?
C34 C32 C33 F31 -79.5(2) . . . . ?
C35 C32 C33 F31 40.7(2) . . . . ?
O31 C32 C33 F33 -85.4(2) . . . . ?
C34 C32 C33 F33 41.3(2) . . . . ?
C35 C32 C33 F33 161.55(17) . . . . ?
O31 C32 C33 F32 32.9(3) . . . . ?
C34 C32 C33 F32 159.56(19) . . . . ?
C35 C32 C33 F32 -80.2(2) . . . . ?
O31 C32 C34 F34 -65.9(2) . . . . ?
C35 C32 C34 F34 47.9(2) . . . . ?
C33 C32 C34 F34 168.11(18) . . . . ?
O31 C32 C34 F35 54.2(2) . . . . ?
C35 C32 C34 F35 168.04(18) . . . . ?
C33 C32 C34 F35 -71.8(2) . . . . ?
O31 C32 C34 F36 174.52(17) . . . . ?
C35 C32 C34 F36 -71.7(2) . . . . ?
C33 C32 C34 F36 48.5(2) . . . . ?
O31 C32 C35 F37 46.3(2) . . . . ?
C34 C32 C35 F37 -74.3(2) . . . . ?
C33 C32 C35 F37 165.32(19) . . . . ?
O31 C32 C35 F39 167.70(18) . . . . ?
C34 C32 C35 F39 47.2(3) . . . . ?
C33 C32 C35 F39 -73.2(2) . . . . ?
O31 C32 C35 F38 -72.8(2) . . . . ?
C34 C32 C35 F38 166.69(17) . . . . ?
C33 C32 C35 F38 46.3(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C31 C3 C4 C5 -178.61(17) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 I5 -179.89(14) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
I5 C5 C6 C1 179.17(14) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C11 C1 C6 C5 179.59(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.624
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_sb528_tw_2-H
_database_code_depnum_ccdc_archive 'CCDC 981373'
_audit_update_record             
;
2014-01-14 deposited with the CCDC.
2015-04-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 1-Ethynyl-3,5-bis((perfluorotert.butoxy)methyl)benzene 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H8 F18 O2'
_chemical_formula_sum            'C18 H8 F18 O2'
_chemical_formula_weight         598.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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                   7.0303(4)
_cell_length_b                   11.8119(10)
_cell_length_c                   14.0402(19)
_cell_angle_alpha                68.704(8)
_cell_angle_beta                 79.860(6)
_cell_angle_gamma                74.572(5)
_cell_volume                     1043.05(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    60
_cell_measurement_theta_min      1
_cell_measurement_theta_max      25

_exptl_crystal_description       plates
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_T_max  0.9955
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 dx = 35 mm, 120 sec./deg., 2 deg., 4 sets, 226 frames,
 3208 refl. postref.
;

_diffrn_ambient_temperature      123(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-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3648
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0612
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3648
_reflns_number_gt                2620
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Collect
_computing_cell_refinement       EVALCCD
_computing_data_reduction        EVALCCD
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.
 non-merohedral twin with 2 domains, BASF = 0.244(4) (TwinRotMat,
 Platon, Spek 2003).
;

_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)+(0.0611P)²+2.4720P] 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         3648
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1863
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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
C1 C 0.7841(7) -0.0955(4) 0.5323(4) 0.0223(10) Uani 1 1 d . . .
C11 C 0.8310(7) -0.2291(5) 0.5775(4) 0.0296(12) Uani 1 1 d . . .
C12 C 0.8712(9) -0.3382(6) 0.6151(5) 0.0467(16) Uani 1 1 d . . .
H12 H 0.9037 -0.4263 0.6455 0.056 Uiso 1 1 calc R . .
C2 C 0.7810(6) -0.0210(5) 0.5907(4) 0.0211(10) Uani 1 1 d . . .
H2 H 0.8096 -0.0587 0.6605 0.025 Uiso 1 1 calc R . .
C3 C 0.7361(6) 0.1082(4) 0.5472(4) 0.0205(10) Uani 1 1 d . . .
C31 C 0.7296(7) 0.1885(5) 0.6098(4) 0.0298(12) Uani 1 1 d . . .
H31A H 0.7984 0.1394 0.6728 0.036 Uiso 1 1 calc R . .
H31B H 0.7941 0.2586 0.5698 0.036 Uiso 1 1 calc R . .
O31 O 0.5200(5) 0.2346(3) 0.6360(3) 0.0250(8) Uani 1 1 d . . .
C32 C 0.4570(7) 0.2886(5) 0.7119(4) 0.0264(11) Uani 1 1 d . . .
C33 C 0.2301(8) 0.3003(5) 0.7255(4) 0.0332(13) Uani 1 1 d . . .
F31 F 0.1366(5) 0.3763(3) 0.7788(3) 0.0435(8) Uani 1 1 d . . .
F32 F 0.1555(5) 0.3443(4) 0.6364(3) 0.0480(9) Uani 1 1 d . . .
F33 F 0.1880(5) 0.1899(3) 0.7757(3) 0.0520(10) Uani 1 1 d . . .
C34 C 0.5034(9) 0.4196(6) 0.6782(6) 0.0489(17) Uani 1 1 d . . .
F34 F 0.6919(6) 0.4176(4) 0.6421(4) 0.0715(13) Uani 1 1 d . . .
F35 F 0.3926(7) 0.4993(3) 0.6043(3) 0.0701(12) Uani 1 1 d . . .
F36 F 0.4680(6) 0.4650(4) 0.7550(4) 0.0759(14) Uani 1 1 d . . .
C35 C 0.5469(9) 0.2063(7) 0.8152(5) 0.0463(16) Uani 1 1 d . . .
F37 F 0.7286(5) 0.2195(4) 0.8153(3) 0.0656(12) Uani 1 1 d . . .
F38 F 0.5608(6) 0.0866(4) 0.8299(3) 0.0626(11) Uani 1 1 d . . .
F39 F 0.4369(6) 0.2330(5) 0.8942(3) 0.0778(15) Uani 1 1 d . . .
C4 C 0.6908(7) 0.1625(4) 0.4454(4) 0.0218(10) Uani 1 1 d . . .
H4 H 0.6573 0.2507 0.4159 0.026 Uiso 1 1 calc R . .
C5 C 0.6941(6) 0.0894(5) 0.3864(3) 0.0205(10) Uani 1 1 d . . .
C51 C 0.6489(7) 0.1497(5) 0.2765(4) 0.0272(11) Uani 1 1 d . . .
H51A H 0.6391 0.0868 0.2474 0.033 Uiso 1 1 calc R . .
H51B H 0.5224 0.2127 0.2702 0.033 Uiso 1 1 calc R . .
O51 O 0.8147(5) 0.2084(3) 0.2235(2) 0.0272(8) Uani 1 1 d . . .
C52 C 0.8602(7) 0.2396(4) 0.1183(3) 0.0222(10) Uani 1 1 d . . .
C53 C 0.7001(8) 0.3454(5) 0.0572(4) 0.0299(12) Uani 1 1 d . . .
F51 F 0.5212(4) 0.3196(3) 0.0856(2) 0.0395(8) Uani 1 1 d . . .
F52 F 0.6918(5) 0.4512(3) 0.0716(3) 0.0448(8) Uani 1 1 d . . .
F53 F 0.7346(5) 0.3651(3) -0.0435(2) 0.0424(8) Uani 1 1 d . . .
C54 C 1.0556(8) 0.2851(5) 0.1008(4) 0.0309(12) Uani 1 1 d . . .
F54 F 1.1035(4) 0.3430(3) 0.0022(2) 0.0364(7) Uani 1 1 d . . .
F55 F 1.0420(5) 0.3632(3) 0.1501(2) 0.0434(8) Uani 1 1 d . . .
F56 F 1.2048(4) 0.1885(3) 0.1345(3) 0.0452(9) Uani 1 1 d . . .
C55 C 0.9000(8) 0.1245(5) 0.0821(4) 0.0332(13) Uani 1 1 d . . .
F57 F 0.7313(5) 0.1039(3) 0.0673(2) 0.0393(8) Uani 1 1 d . . .
F58 F 0.9858(5) 0.0228(3) 0.1532(3) 0.0455(9) Uani 1 1 d . . .
F59 F 1.0162(5) 0.1378(3) -0.0049(3) 0.0492(9) Uani 1 1 d . . .
C6 C 0.7396(7) -0.0386(5) 0.4303(4) 0.0230(11) Uani 1 1 d . . .
H6 H 0.7407 -0.0888 0.3904 0.028 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.395(7) . ?
C1 C2 1.399(7) . ?
C1 C11 1.440(7) . ?
C11 C12 1.176(8) . ?
C12 H12 0.9500 . ?
C2 C3 1.391(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(7) . ?
C3 C31 1.498(7) . ?
C31 O31 1.460(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
O31 C32 1.384(6) . ?
C32 C33 1.548(7) . ?
C32 C34 1.551(8) . ?
C32 C35 1.556(8) . ?
C33 F32 1.313(6) . ?
C33 F33 1.323(6) . ?
C33 F31 1.341(6) . ?
C34 F35 1.324(8) . ?
C34 F36 1.329(7) . ?
C34 F34 1.329(7) . ?
C35 F39 1.322(7) . ?
C35 F37 1.328(7) . ?
C35 F38 1.331(8) . ?
C4 C5 1.392(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(7) . ?
C5 C51 1.498(7) . ?
C51 O51 1.464(6) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
O51 C52 1.386(5) . ?
C52 C53 1.542(7) . ?
C52 C54 1.554(7) . ?
C52 C55 1.561(7) . ?
C53 F52 1.322(6) . ?
C53 F51 1.331(6) . ?
C53 F53 1.336(6) . ?
C54 F55 1.315(6) . ?
C54 F54 1.330(6) . ?
C54 F56 1.331(6) . ?
C55 F58 1.325(6) . ?
C55 F59 1.326(6) . ?
C55 F57 1.336(6) . ?
C6 H6 0.9500 . ?

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
C6 C1 C2 119.1(4) . . ?
C6 C1 C11 120.7(4) . . ?
C2 C1 C11 120.2(5) . . ?
C12 C11 C1 179.1(6) . . ?
C11 C12 H12 180.0 . . ?
C3 C2 C1 120.3(4) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.3(4) . . ?
C2 C3 C31 120.5(4) . . ?
C4 C3 C31 120.1(4) . . ?
O31 C31 C3 105.9(4) . . ?
O31 C31 H31A 110.6 . . ?
C3 C31 H31A 110.6 . . ?
O31 C31 H31B 110.6 . . ?
C3 C31 H31B 110.6 . . ?
H31A C31 H31B 108.7 . . ?
C32 O31 C31 121.9(4) . . ?
O31 C32 C33 103.3(4) . . ?
O31 C32 C34 111.8(4) . . ?
C33 C32 C34 109.8(4) . . ?
O31 C32 C35 112.7(4) . . ?
C33 C32 C35 109.7(4) . . ?
C34 C32 C35 109.3(5) . . ?
F32 C33 F33 108.0(5) . . ?
F32 C33 F31 107.6(4) . . ?
F33 C33 F31 107.6(4) . . ?
F32 C33 C32 111.3(4) . . ?
F33 C33 C32 110.2(4) . . ?
F31 C33 C32 112.0(4) . . ?
F35 C34 F36 107.4(5) . . ?
F35 C34 F34 107.5(6) . . ?
F36 C34 F34 107.6(5) . . ?
F35 C34 C32 110.4(5) . . ?
F36 C34 C32 112.2(5) . . ?
F34 C34 C32 111.6(5) . . ?
F39 C35 F37 108.3(5) . . ?
F39 C35 F38 108.2(6) . . ?
F37 C35 F38 106.9(5) . . ?
F39 C35 C32 111.8(5) . . ?
F37 C35 C32 111.6(5) . . ?
F38 C35 C32 109.9(5) . . ?
C5 C4 C3 120.9(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 119.2(4) . . ?
C6 C5 C51 120.7(4) . . ?
C4 C5 C51 120.0(4) . . ?
O51 C51 C5 105.2(4) . . ?
O51 C51 H51A 110.7 . . ?
C5 C51 H51A 110.7 . . ?
O51 C51 H51B 110.7 . . ?
C5 C51 H51B 110.7 . . ?
H51A C51 H51B 108.8 . . ?
C52 O51 C51 122.3(3) . . ?
O51 C52 C53 112.6(4) . . ?
O51 C52 C54 103.1(4) . . ?
C53 C52 C54 109.7(4) . . ?
O51 C52 C55 112.0(4) . . ?
C53 C52 C55 110.1(4) . . ?
C54 C52 C55 109.0(4) . . ?
F52 C53 F51 107.6(4) . . ?
F52 C53 F53 107.6(4) . . ?
F51 C53 F53 106.9(4) . . ?
F52 C53 C52 111.0(4) . . ?
F51 C53 C52 111.5(4) . . ?
F53 C53 C52 112.0(4) . . ?
F55 C54 F54 107.4(4) . . ?
F55 C54 F56 108.2(4) . . ?
F54 C54 F56 107.4(4) . . ?
F55 C54 C52 111.3(4) . . ?
F54 C54 C52 112.4(4) . . ?
F56 C54 C52 110.0(4) . . ?
F58 C55 F59 108.2(4) . . ?
F58 C55 F57 107.0(4) . . ?
F59 C55 F57 107.6(4) . . ?
F58 C55 C52 110.1(4) . . ?
F59 C55 C52 112.5(4) . . ?
F57 C55 C52 111.3(4) . . ?
C5 C6 C1 121.1(4) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?

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
C6 C1 C11 C12 141(47) . . . . ?
C2 C1 C11 C12 -39(47) . . . . ?
C6 C1 C2 C3 -0.7(7) . . . . ?
C11 C1 C2 C3 179.9(4) . . . . ?
C1 C2 C3 C4 1.2(6) . . . . ?
C1 C2 C3 C31 179.1(4) . . . . ?
C2 C3 C31 O31 -102.6(5) . . . . ?
C4 C3 C31 O31 75.3(5) . . . . ?
C3 C31 O31 C32 165.2(4) . . . . ?
C31 O31 C32 C33 -170.2(4) . . . . ?
C31 O31 C32 C34 71.7(6) . . . . ?
C31 O31 C32 C35 -51.8(6) . . . . ?
O31 C32 C33 F32 -45.2(5) . . . . ?
C34 C32 C33 F32 74.2(6) . . . . ?
C35 C32 C33 F32 -165.6(5) . . . . ?
O31 C32 C33 F33 74.6(5) . . . . ?
C34 C32 C33 F33 -166.0(5) . . . . ?
C35 C32 C33 F33 -45.8(6) . . . . ?
O31 C32 C33 F31 -165.7(4) . . . . ?
C34 C32 C33 F31 -46.3(6) . . . . ?
C35 C32 C33 F31 73.9(6) . . . . ?
O31 C32 C34 F35 68.7(6) . . . . ?
C33 C32 C34 F35 -45.4(6) . . . . ?
C35 C32 C34 F35 -165.8(5) . . . . ?
O31 C32 C34 F36 -171.6(5) . . . . ?
C33 C32 C34 F36 74.3(6) . . . . ?
C35 C32 C34 F36 -46.0(6) . . . . ?
O31 C32 C34 F34 -50.8(7) . . . . ?
C33 C32 C34 F34 -164.9(5) . . . . ?
C35 C32 C34 F34 74.7(7) . . . . ?
O31 C32 C35 F39 -156.9(5) . . . . ?
C33 C32 C35 F39 -42.3(7) . . . . ?
C34 C32 C35 F39 78.2(7) . . . . ?
O31 C32 C35 F37 81.7(6) . . . . ?
C33 C32 C35 F37 -163.8(4) . . . . ?
C34 C32 C35 F37 -43.3(6) . . . . ?
O31 C32 C35 F38 -36.8(6) . . . . ?
C33 C32 C35 F38 77.8(5) . . . . ?
C34 C32 C35 F38 -161.7(5) . . . . ?
C2 C3 C4 C5 -1.4(6) . . . . ?
C31 C3 C4 C5 -179.3(4) . . . . ?
C3 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 C51 -178.8(4) . . . . ?
C6 C5 C51 O51 -111.9(5) . . . . ?
C4 C5 C51 O51 68.0(5) . . . . ?
C5 C51 O51 C52 159.4(4) . . . . ?
C51 O51 C52 C53 67.5(6) . . . . ?
C51 O51 C52 C54 -174.4(4) . . . . ?
C51 O51 C52 C55 -57.3(6) . . . . ?
O51 C52 C53 F52 66.7(5) . . . . ?
C54 C52 C53 F52 -47.5(5) . . . . ?
C55 C52 C53 F52 -167.5(4) . . . . ?
O51 C52 C53 F51 -53.3(6) . . . . ?
C54 C52 C53 F51 -167.5(4) . . . . ?
C55 C52 C53 F51 72.5(5) . . . . ?
O51 C52 C53 F53 -173.1(4) . . . . ?
C54 C52 C53 F53 72.7(5) . . . . ?
C55 C52 C53 F53 -47.2(5) . . . . ?
O51 C52 C54 F55 -46.9(5) . . . . ?
C53 C52 C54 F55 73.3(5) . . . . ?
C55 C52 C54 F55 -166.0(4) . . . . ?
O51 C52 C54 F54 -167.3(4) . . . . ?
C53 C52 C54 F54 -47.1(6) . . . . ?
C55 C52 C54 F54 73.5(5) . . . . ?
O51 C52 C54 F56 73.1(5) . . . . ?
C53 C52 C54 F56 -166.8(4) . . . . ?
C55 C52 C54 F56 -46.1(5) . . . . ?
O51 C52 C55 F58 -34.0(6) . . . . ?
C53 C52 C55 F58 -160.1(4) . . . . ?
C54 C52 C55 F58 79.5(5) . . . . ?
O51 C52 C55 F59 -154.7(4) . . . . ?
C53 C52 C55 F59 79.2(5) . . . . ?
C54 C52 C55 F59 -41.2(6) . . . . ?
O51 C52 C55 F57 84.5(5) . . . . ?
C53 C52 C55 F57 -41.6(5) . . . . ?
C54 C52 C55 F57 -162.0(4) . . . . ?
C4 C5 C6 C1 -0.6(7) . . . . ?
C51 C5 C6 C1 179.3(4) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
C11 C1 C6 C5 179.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.085

#==============================================================================

#_eof # End of Crystallographic Information File

