# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dawson03
_database_code_depnum_ccdc_archive 'CCDC 1531817'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_audit_creation_date             2016-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H11 F9 O4'
_chemical_formula_sum            'C11 H11 F9 O4'
_chemical_formula_weight         378.20
_chemical_absolute_configuration .
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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'

_cell_length_a                   8.2625(4)
_cell_length_b                   9.6405(4)
_cell_length_c                   17.8895(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1424.98(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8166
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.59
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  0.6466
_exptl_absorpt_correction_T_min  0.5900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0670 after correction.
The Ratio of minimum to maximum transmission is 0.9125.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17826
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.748
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                2776
_reflns_number_total             3022
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1112 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.3106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0741
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F8 F 0.08475(18) 0.30589(16) 0.79682(8) 0.0294(4) Uani 1 1 d . . . . .
F9 F -0.11525(17) 0.32665(16) 0.72164(8) 0.0286(3) Uani 1 1 d . . . . .
F6 F 0.02677(19) 0.58373(16) 0.46508(8) 0.0333(4) Uani 1 1 d . . . . .
F5 F 0.2790(2) 0.61384(16) 0.43931(8) 0.0312(4) Uani 1 1 d . . . . .
F7 F 0.0003(2) 0.50932(15) 0.76511(8) 0.0324(4) Uani 1 1 d . . . . .
F1 F 0.6213(2) 0.53382(17) 0.73549(9) 0.0349(4) Uani 1 1 d . . . . .
F4 F 0.1671(2) 0.73013(15) 0.52855(9) 0.0344(4) Uani 1 1 d . . . . .
F2 F 0.4837(2) 0.69738(15) 0.68343(9) 0.0339(4) Uani 1 1 d . . . . .
F3 F 0.67525(19) 0.59711(18) 0.62236(9) 0.0359(4) Uani 1 1 d . . . . .
O3 O 0.18296(19) 0.24196(16) 0.65403(9) 0.0178(3) Uani 1 1 d . . . . .
O2 O 0.2227(2) 0.36421(16) 0.51158(9) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.2984 0.3668 0.4803 0.030 Uiso 1 1 calc GR . . . .
O1 O 0.3688(2) 0.53225(17) 0.57726(9) 0.0209(4) Uani 1 1 d . . . . .
O4 O -0.0467(2) 0.20135(17) 0.58867(9) 0.0223(4) Uani 1 1 d . . . . .
C10 C 0.0887(3) 0.1677(2) 0.60639(13) 0.0190(5) Uani 1 1 d . . . . .
C2 C 0.0879(3) 0.4768(2) 0.61102(13) 0.0185(5) Uani 1 1 d . . . . .
H2A H -0.0122 0.4368 0.5896 0.022 Uiso 1 1 calc R . . . .
H2B H 0.0619 0.5701 0.6308 0.022 Uiso 1 1 calc R . . . .
C9 C 0.0273(3) 0.3803(2) 0.73943(14) 0.0225(5) Uani 1 1 d . . . . .
C4 C 0.3087(3) 0.4424(2) 0.70394(14) 0.0204(5) Uani 1 1 d . . . . .
H4A H 0.3535 0.3777 0.7416 0.024 Uiso 1 1 calc R . . . .
H4B H 0.2879 0.5321 0.7292 0.024 Uiso 1 1 calc R . . . .
C1 C 0.2162(3) 0.4893(2) 0.55012(14) 0.0184(5) Uani 1 1 d . . . . .
C3 C 0.1483(3) 0.3843(2) 0.67482(13) 0.0179(5) Uani 1 1 d . . . . .
C8 C 0.1715(3) 0.6057(2) 0.49541(14) 0.0233(5) Uani 1 1 d . . . . .
C6 C 0.5290(3) 0.3341(2) 0.62090(15) 0.0234(5) Uani 1 1 d . . . . .
H6A H 0.4542 0.2647 0.6006 0.035 Uiso 1 1 calc GR . . . .
H6B H 0.5828 0.2964 0.6653 0.035 Uiso 1 1 calc GR . . . .
H6C H 0.6103 0.3574 0.5831 0.035 Uiso 1 1 calc GR . . . .
C5 C 0.4347(3) 0.4647(2) 0.64231(14) 0.0209(5) Uani 1 1 d . . . . .
C7 C 0.5548(3) 0.5743(3) 0.67066(15) 0.0267(6) Uani 1 1 d . . . . .
C11 C 0.1754(3) 0.0407(2) 0.58122(14) 0.0252(5) Uani 1 1 d . . . . .
H11A H 0.2572 0.0659 0.5439 0.038 Uiso 1 1 calc GR . . . .
H11B H 0.0979 -0.0243 0.5590 0.038 Uiso 1 1 calc GR . . . .
H11C H 0.2283 -0.0033 0.6241 0.038 Uiso 1 1 calc GR . . . .


_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
F8 C9 1.339(3) . ?
F9 C9 1.325(3) . ?
F6 C8 1.330(3) . ?
F5 C8 1.342(3) . ?
F7 C9 1.345(3) . ?
F1 C7 1.341(3) . ?
F4 C8 1.338(3) . ?
F2 C7 1.344(3) . ?
F3 C7 1.336(3) . ?
O3 C10 1.359(3) . ?
O3 C3 1.450(3) . ?
O2 H2 0.8400 . ?
O2 C1 1.390(3) . ?
O1 C1 1.413(3) . ?
O1 C5 1.440(3) . ?
O4 C10 1.207(3) . ?
C10 C11 1.489(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.525(3) . ?
C2 C3 1.532(3) . ?
C9 C3 1.528(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.531(3) . ?
C4 C5 1.531(4) . ?
C1 C8 1.534(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C6 C5 1.529(3) . ?
C5 C7 1.537(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O3 C3 123.09(18) . . ?
C1 O2 H2 109.5 . . ?
C1 O1 C5 118.80(18) . . ?
O3 C10 C11 110.3(2) . . ?
O4 C10 O3 123.7(2) . . ?
O4 C10 C11 126.0(2) . . ?
H2A C2 H2B 108.1 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 C3 110.62(18) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
F8 C9 F7 106.99(19) . . ?
F8 C9 C3 111.2(2) . . ?
F9 C9 F8 106.86(19) . . ?
F9 C9 F7 107.18(19) . . ?
F9 C9 C3 114.2(2) . . ?
F7 C9 C3 110.10(19) . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.3(2) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
O2 C1 O1 112.96(19) . . ?
O2 C1 C2 108.23(18) . . ?
O2 C1 C8 109.11(19) . . ?
O1 C1 C2 113.45(19) . . ?
O1 C1 C8 102.67(18) . . ?
C2 C1 C8 110.27(19) . . ?
O3 C3 C2 115.10(18) . . ?
O3 C3 C9 107.42(18) . . ?
O3 C3 C4 105.23(18) . . ?
C9 C3 C2 111.43(19) . . ?
C9 C3 C4 108.54(19) . . ?
C4 C3 C2 108.79(19) . . ?
F6 C8 F5 107.4(2) . . ?
F6 C8 F4 107.4(2) . . ?
F6 C8 C1 111.09(19) . . ?
F5 C8 C1 111.1(2) . . ?
F4 C8 F5 107.3(2) . . ?
F4 C8 C1 112.3(2) . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
O1 C5 C4 112.9(2) . . ?
O1 C5 C6 111.2(2) . . ?
O1 C5 C7 101.50(18) . . ?
C4 C5 C7 107.3(2) . . ?
C6 C5 C4 114.3(2) . . ?
C6 C5 C7 108.6(2) . . ?
F1 C7 F2 106.8(2) . . ?
F1 C7 C5 110.5(2) . . ?
F2 C7 C5 112.4(2) . . ?
F3 C7 F1 107.6(2) . . ?
F3 C7 F2 106.9(2) . . ?
F3 C7 C5 112.4(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dawson01_a
_database_code_depnum_ccdc_archive 'CCDC 1531815'
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2017-05-30 downloaded from the CCDC.
;
_audit_creation_date             2016-01-28
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 F9 O3'
_chemical_formula_sum            'C9 H9 F9 O3'
_chemical_formula_weight         336.16
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   7.8200(13)
_cell_length_b                   9.4398(16)
_cell_length_c                   16.743(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.709(9)
_cell_angle_gamma                90
_cell_volume                     1224.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3905
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.933
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1146 before and 0.0565 after correction.
The Ratio of minimum to maximum transmission is 0.8397.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.823
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12258
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.336
_diffrn_reflns_theta_min         2.455
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2287
_reflns_number_total             3040
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3040
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1002
_refine_ls_wR_factor_ref         0.1080
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
F1 F 0.39743(13) 0.73752(9) 0.65350(6) 0.0269(2) Uani 1 1 d . . . . .
F2 F 0.17806(13) 0.67303(9) 0.56942(6) 0.0270(2) Uani 1 1 d . . . . .
F3 F 0.43503(13) 0.63929(9) 0.54073(6) 0.0281(2) Uani 1 1 d . . . . .
F9 F 0.85197(12) 0.41867(10) 0.73353(7) 0.0319(3) Uani 1 1 d . . . . .
F8 F 0.82519(13) 0.19513(10) 0.70717(7) 0.0320(3) Uani 1 1 d . . . . .
F4 F 0.04703(13) 0.14156(10) 0.53265(7) 0.0348(3) Uani 1 1 d . . . . .
F6 F 0.23064(13) -0.00864(9) 0.59061(6) 0.0324(3) Uani 1 1 d . . . . .
F7 F 0.78874(13) 0.34887(11) 0.61092(7) 0.0323(3) Uani 1 1 d . . . . .
F5 F 0.29528(15) 0.11934(11) 0.49215(6) 0.0353(3) Uani 1 1 d . . . . .
O3 O 0.51665(13) 0.46566(10) 0.66586(7) 0.0203(3) Uani 1 1 d . . . . .
O1 O 0.24456(15) 0.50544(12) 0.70601(7) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.18915(15) 0.22603(13) 0.68402(8) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.2577(2) 0.38035(14) 0.58113(10) 0.0182(3) Uani 1 1 d . . . . .
H2A H 0.3105 0.3856 0.5307 0.022 Uiso 1 1 calc R . . . .
H2B H 0.1325 0.3988 0.5679 0.022 Uiso 1 1 calc R . . . .
C7 C 0.3381(2) 0.63713(15) 0.60085(10) 0.0208(3) Uani 1 1 d . . . . .
C1 C 0.3392(2) 0.49086(15) 0.64090(9) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.4785(2) 0.20762(14) 0.64357(10) 0.0190(3) Uani 1 1 d . . . . .
H4A H 0.5356 0.1978 0.5945 0.023 Uiso 1 1 calc R . . . .
H4B H 0.4935 0.1172 0.6736 0.023 Uiso 1 1 calc R . . . .
C3 C 0.28681(19) 0.23357(14) 0.61859(10) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.5680(2) 0.32686(15) 0.69646(10) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.2145(2) 0.12081(16) 0.55771(11) 0.0244(4) Uani 1 1 d . . . . .
C9 C 0.7595(2) 0.32302(17) 0.68668(11) 0.0247(4) Uani 1 1 d . . . . .
C6 C 0.5514(2) 0.31311(16) 0.78599(10) 0.0236(4) Uani 1 1 d . . . . .
H6A H 0.6043 0.3957 0.8150 0.035 Uiso 1 1 calc GR . . . .
H6B H 0.6102 0.2268 0.8075 0.035 Uiso 1 1 calc GR . . . .
H6C H 0.4291 0.3081 0.7929 0.035 Uiso 1 1 calc GR . . . .
H2 H 0.211(4) 0.160(3) 0.7109(19) 0.088(11) Uiso 1 1 d . . . . .
H1 H 0.204(4) 0.441(3) 0.7149(19) 0.090(12) Uiso 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
F1 C7 1.3345(18) . ?
F2 C7 1.3346(19) . ?
F3 C7 1.3390(19) . ?
F9 C9 1.3421(19) . ?
F8 C9 1.3386(18) . ?
F4 C8 1.3348(19) . ?
F6 C8 1.3394(18) . ?
F7 C9 1.341(2) . ?
F5 C8 1.338(2) . ?
O3 C1 1.4150(18) . ?
O3 C5 1.4440(17) . ?
O1 C1 1.4039(19) . ?
O1 H1 0.71(3) . ?
O2 C3 1.419(2) . ?
O2 H2 0.77(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.525(2) . ?
C2 C3 1.5254(19) . ?
C7 C1 1.535(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.521(2) . ?
C4 C5 1.541(2) . ?
C3 C8 1.529(2) . ?
C5 C9 1.528(2) . ?
C5 C6 1.528(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O3 C5 118.20(11) . . ?
C1 O1 H1 112(3) . . ?
C3 O2 H2 113(2) . . ?
H2A C2 H2B 108.3 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
C1 C2 C3 108.99(12) . . ?
C3 C2 H2A 109.9 . . ?
C3 C2 H2B 109.9 . . ?
F1 C7 F2 107.74(12) . . ?
F1 C7 F3 107.70(12) . . ?
F1 C7 C1 111.67(13) . . ?
F2 C7 F3 107.17(13) . . ?
F2 C7 C1 110.52(13) . . ?
F3 C7 C1 111.82(12) . . ?
O3 C1 C2 112.69(12) . . ?
O3 C1 C7 103.18(12) . . ?
O1 C1 O3 112.66(12) . . ?
O1 C1 C2 111.07(12) . . ?
O1 C1 C7 106.18(12) . . ?
C2 C1 C7 110.58(13) . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.29(12) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
O2 C3 C2 107.27(12) . . ?
O2 C3 C4 113.10(13) . . ?
O2 C3 C8 106.89(12) . . ?
C2 C3 C8 109.68(13) . . ?
C4 C3 C2 110.28(12) . . ?
C4 C3 C8 109.51(12) . . ?
O3 C5 C4 112.05(12) . . ?
O3 C5 C9 102.32(12) . . ?
O3 C5 C6 111.66(12) . . ?
C9 C5 C4 107.29(12) . . ?
C6 C5 C4 114.20(12) . . ?
C6 C5 C9 108.46(13) . . ?
F4 C8 F6 107.32(13) . . ?
F4 C8 F5 107.16(13) . . ?
F4 C8 C3 111.53(12) . . ?
F6 C8 C3 110.79(13) . . ?
F5 C8 F6 107.40(12) . . ?
F5 C8 C3 112.39(13) . . ?
F9 C9 C5 112.34(13) . . ?
F8 C9 F9 107.39(13) . . ?
F8 C9 F7 107.36(14) . . ?
F8 C9 C5 109.98(13) . . ?
F7 C9 F9 106.47(13) . . ?
F7 C9 C5 113.00(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C7 C1 O3 -63.75(15) . . . . ?
F1 C7 C1 O1 54.93(16) . . . . ?
F1 C7 C1 C2 175.51(12) . . . . ?
F2 C7 C1 O3 176.33(12) . . . . ?
F2 C7 C1 O1 -64.99(16) . . . . ?
F2 C7 C1 C2 55.59(17) . . . . ?
F3 C7 C1 O3 57.02(16) . . . . ?
F3 C7 C1 O1 175.71(12) . . . . ?
F3 C7 C1 C2 -63.71(16) . . . . ?
O3 C5 C9 F9 65.01(16) . . . . ?
O3 C5 C9 F8 -175.44(13) . . . . ?
O3 C5 C9 F7 -55.49(16) . . . . ?
O2 C3 C8 F4 58.61(16) . . . . ?
O2 C3 C8 F6 -60.86(16) . . . . ?
O2 C3 C8 F5 178.98(12) . . . . ?
C2 C3 C8 F4 -57.37(17) . . . . ?
C2 C3 C8 F6 -176.85(13) . . . . ?
C2 C3 C8 F5 62.99(16) . . . . ?
C1 O3 C5 C4 45.12(17) . . . . ?
C1 O3 C5 C9 159.75(12) . . . . ?
C1 O3 C5 C6 -84.43(16) . . . . ?
C1 C2 C3 O2 67.31(15) . . . . ?
C1 C2 C3 C4 -56.26(16) . . . . ?
C1 C2 C3 C8 -176.94(13) . . . . ?
C4 C3 C8 F4 -178.53(13) . . . . ?
C4 C3 C8 F6 62.00(17) . . . . ?
C4 C3 C8 F5 -58.16(16) . . . . ?
C4 C5 C9 F9 -176.92(12) . . . . ?
C4 C5 C9 F8 -57.37(16) . . . . ?
C4 C5 C9 F7 62.58(16) . . . . ?
C3 C2 C1 O3 56.13(16) . . . . ?
C3 C2 C1 O1 -71.36(15) . . . . ?
C3 C2 C1 C7 171.03(12) . . . . ?
C3 C4 C5 O3 -44.32(18) . . . . ?
C3 C4 C5 C9 -155.86(13) . . . . ?
C3 C4 C5 C6 83.90(16) . . . . ?
C5 O3 C1 O1 74.44(15) . . . . ?
C5 O3 C1 C2 -52.20(17) . . . . ?
C5 O3 C1 C7 -171.49(12) . . . . ?
C5 C4 C3 O2 -68.33(16) . . . . ?
C5 C4 C3 C2 51.79(17) . . . . ?
C5 C4 C3 C8 172.58(13) . . . . ?
C6 C5 C9 F9 -53.10(16) . . . . ?
C6 C5 C9 F8 66.45(16) . . . . ?
C6 C5 C9 F7 -173.61(12) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
