# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cs854
_database_code_depnum_ccdc_archive 'CCDC 1939200'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille universite
France
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2019-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H13 F9 O2'
_chemical_formula_sum            'C11 H13 F9 O2'
_chemical_formula_weight         348.21
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.60440(10)
_cell_length_b                   9.5819(2)
_cell_length_c                   26.4720(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1421.57(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13313
_cell_measurement_temperature    295
_cell_measurement_theta_max      70.9350
_cell_measurement_theta_min      4.8860
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.628
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19917
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.062
_diffrn_reflns_theta_min         3.339
_diffrn_ambient_temperature      295
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00-180.00  109
  2  ω   -115.00 -17.00   1.00    1.00    --  -41.07 -38.00-120.00   98
  3  ω     28.00 117.00   1.00   10.00    --  101.41-125.00  60.00   89
  4  ω     73.00 178.00   1.00   10.00    --  101.41  30.00 120.00  105
  5  ω     28.00 117.00   1.00   10.00    --  101.41-125.00-180.00   89
  6  ω     94.00 175.00   1.00   10.00    --  101.41 125.00  90.00   81
  7  ω     28.00 127.00   1.00   10.00    --  101.41 -45.00-180.00   99
  8  ω   -117.00  -8.00   1.00    1.00    --  -41.07 -77.00  30.00  109
  9  ω     23.00  97.00   1.00    1.00    --   41.07-125.00-120.00   74
 10  ω     72.00 174.00   1.00   10.00    --  101.41  61.00-150.00  102
 11  ω     72.00 174.00   1.00   10.00    --  101.41  61.00  30.00  102
 12  ω     76.00 174.00   1.00   10.00    --  101.41  45.00 -90.00   98
 13  ω     76.00 174.00   1.00   10.00    --  101.41  45.00 -30.00   98
 14  ω   -113.00 -13.00   1.00    1.00    --  -41.07 -57.00  90.00  100
 15  ω      1.00  82.00   1.00    1.00    --   41.07 -99.00  30.00   81
 16  ω     69.00 178.00   1.00   10.00    --  101.41  77.00 150.00  109
 17  ω     94.00 175.00   1.00   10.00    --  101.41 125.00-150.00   81
 18  ω     72.00 174.00   1.00   10.00    --  101.41  61.00   0.00  102
 19  ω     19.00 109.00   1.00   10.00    --  101.41 -94.00-150.00   90
 20  ω      8.00 117.00   1.00    1.00    --   41.07  77.00 -30.00  109
 21  ω      1.00  82.00   1.00    1.00    --   41.07 -99.00 -60.00   81
 22  ω     72.00 174.00   1.00   10.00    --  101.41  61.00  60.00  102
 23  ω     72.00 174.00   1.00   10.00    --  101.41  61.00 120.00  102
 24  ω     69.00 101.00   1.00   10.00    --  101.41  77.00-180.00   32
 25  ω     69.00 178.00   1.00   10.00    --  101.41  77.00 -90.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0700226000
_diffrn_orient_matrix_UB_12      -0.1551270000
_diffrn_orient_matrix_UB_13      -0.0040102000
_diffrn_orient_matrix_UB_21      -0.0030974000
_diffrn_orient_matrix_UB_22      0.0118252000
_diffrn_orient_matrix_UB_23      -0.0580147000
_diffrn_orient_matrix_UB_31      0.2658026000
_diffrn_orient_matrix_UB_32      -0.0407487000
_diffrn_orient_matrix_UB_33      -0.0017169000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.682
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                2630
_reflns_number_total             2746
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1006 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2746
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.064
_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)+(0.0878P)²+0.3453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1393
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
2.d 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
F1 F 0.8629(3) 0.5102(3) 0.51030(8) 0.0628(6) Uani 1 1 d . . . . .
F2 F 0.6046(5) 0.6754(2) 0.49805(8) 0.0627(6) Uani 1 1 d . . . . .
F3 F 0.3099(4) 0.5222(4) 0.56901(9) 0.0870(9) Uani 1 1 d . . . . .
F4 F 0.6378(7) 0.4122(2) 0.58771(8) 0.0813(8) Uani 1 1 d . . . . .
F5 F 0.8545(6) 0.6785(4) 0.59565(12) 0.1030(11) Uani 1 1 d . . . . .
F6 F 0.5024(8) 0.7650(3) 0.59036(11) 0.1079(13) Uani 1 1 d . . . . .
F7 F 0.3678(10) 0.5966(7) 0.66797(14) 0.172(3) Uani 1 1 d . . . . .
F8 F 0.7245(13) 0.5319(4) 0.67593(12) 0.175(3) Uani 1 1 d . . . . .
F9 F 0.6357(7) 0.7412(3) 0.68456(11) 0.1038(11) Uani 1 1 d . . . . .
O1 O 0.2047(4) 0.4020(4) 0.39220(10) 0.0669(7) Uani 1 1 d . . . . .
O2 O 0.5210(6) 0.3082(3) 0.48975(10) 0.0662(7) Uani 1 1 d . . . . .
H2 H 0.390132 0.273155 0.495282 0.099 Uiso 1 1 calc GR . . . .
C1 C 0.5148(6) 0.3851(4) 0.32969(12) 0.0539(8) Uani 1 1 d . . . . .
C2 C 0.4134(5) 0.4160(4) 0.38229(11) 0.0460(7) Uani 1 1 d . . . . .
C3 C 0.5848(5) 0.4704(4) 0.42198(11) 0.0490(7) Uani 1 1 d . . . . .
H3A H 0.611386 0.569221 0.416461 0.059 Uiso 1 1 calc R . . . .
H3B H 0.736798 0.422993 0.418429 0.059 Uiso 1 1 calc R . . . .
C4 C 0.4912(6) 0.4484(3) 0.47515(11) 0.0455(7) Uani 1 1 d . . . . .
H4 H 0.321316 0.472447 0.476288 0.055 Uiso 1 1 calc R . . . .
C5 C 0.6272(5) 0.5400(3) 0.51209(11) 0.0415(6) Uani 1 1 d . . . . .
C6 C 0.5476(6) 0.5287(4) 0.56783(11) 0.0473(7) Uani 1 1 d . . . . .
C7 C 0.6247(7) 0.6519(4) 0.60230(14) 0.0553(8) Uani 1 1 d . . . . .
C8 C 0.5868(11) 0.6288(5) 0.65892(15) 0.0764(13) Uani 1 1 d . . . . .
C9 C 0.3106(8) 0.3607(7) 0.29279(17) 0.0863(16) Uani 1 1 d . . . . .
H9A H 0.207411 0.289138 0.305733 0.129 Uiso 1 1 calc GR . . . .
H9B H 0.373875 0.331960 0.260736 0.129 Uiso 1 1 calc GR . . . .
H9C H 0.221708 0.445557 0.288638 0.129 Uiso 1 1 calc GR . . . .
C10 C 0.6716(9) 0.5048(5) 0.31254(15) 0.0717(11) Uani 1 1 d . . . . .
H10A H 0.583254 0.590453 0.314360 0.108 Uiso 1 1 calc GR . . . .
H10B H 0.721763 0.488964 0.278337 0.108 Uiso 1 1 calc GR . . . .
H10C H 0.809137 0.510726 0.334040 0.108 Uiso 1 1 calc GR . . . .
C11 C 0.6627(8) 0.2513(5) 0.33408(19) 0.0746(11) Uani 1 1 d . . . . .
H11A H 0.794770 0.266947 0.356466 0.112 Uiso 1 1 calc GR . . . .
H11B H 0.721472 0.225410 0.301328 0.112 Uiso 1 1 calc GR . . . .
H11C H 0.564603 0.177567 0.347199 0.112 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
F1 C5 1.352(4) . ?
F2 C5 1.355(4) . ?
F3 C6 1.334(4) . ?
F4 C6 1.334(4) . ?
F5 C7 1.325(5) . ?
F6 C7 1.321(5) . ?
F7 C8 1.288(7) . ?
F8 C8 1.289(6) . ?
F9 C8 1.302(5) . ?
O1 C2 1.206(4) . ?
O2 H2 0.8200 . ?
O2 C4 1.408(4) . ?
C1 C2 1.533(4) . ?
C1 C9 1.523(5) . ?
C1 C10 1.515(6) . ?
C1 C11 1.531(6) . ?
C2 C3 1.516(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.517(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.519(4) . ?
C5 C6 1.545(4) . ?
C6 C7 1.553(5) . ?
C7 C8 1.530(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 H2 109.5 . . ?
C9 C1 C2 109.5(3) . . ?
C9 C1 C11 109.1(4) . . ?
C10 C1 C2 109.9(3) . . ?
C10 C1 C9 111.1(4) . . ?
C10 C1 C11 110.0(4) . . ?
C11 C1 C2 107.1(3) . . ?
O1 C2 C1 122.4(3) . . ?
O1 C2 C3 120.1(3) . . ?
C3 C2 C1 117.5(3) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C2 C3 C4 112.1(3) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
O2 C4 C3 110.3(3) . . ?
O2 C4 H4 109.4 . . ?
O2 C4 C5 108.4(2) . . ?
C3 C4 H4 109.4 . . ?
C3 C4 C5 110.1(2) . . ?
C5 C4 H4 109.4 . . ?
F1 C5 F2 106.5(3) . . ?
F1 C5 C4 110.2(2) . . ?
F1 C5 C6 107.5(2) . . ?
F2 C5 C4 109.2(2) . . ?
F2 C5 C6 107.5(2) . . ?
C4 C5 C6 115.4(2) . . ?
F3 C6 C5 108.3(3) . . ?
F3 C6 C7 107.4(3) . . ?
F4 C6 F3 109.2(3) . . ?
F4 C6 C5 109.0(3) . . ?
F4 C6 C7 107.4(3) . . ?
C5 C6 C7 115.3(3) . . ?
F5 C7 C6 109.8(3) . . ?
F5 C7 C8 107.0(4) . . ?
F6 C7 F5 108.3(4) . . ?
F6 C7 C6 109.8(3) . . ?
F6 C7 C8 106.3(3) . . ?
C8 C7 C6 115.3(3) . . ?
F7 C8 F8 109.4(6) . . ?
F7 C8 F9 107.6(5) . . ?
F7 C8 C7 110.4(4) . . ?
F8 C8 F9 106.7(4) . . ?
F8 C8 C7 111.3(4) . . ?
F9 C8 C7 111.2(4) . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 C11 H11A 109.5 . . ?
C1 C11 H11B 109.5 . . ?
C1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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 C5 C6 F3 -164.4(3) . . . . ?
F1 C5 C6 F4 -45.6(3) . . . . ?
F1 C5 C6 C7 75.2(3) . . . . ?
F2 C5 C6 F3 81.3(3) . . . . ?
F2 C5 C6 F4 -159.9(3) . . . . ?
F2 C5 C6 C7 -39.1(4) . . . . ?
F3 C6 C7 F5 -169.1(3) . . . . ?
F3 C6 C7 F6 -50.1(4) . . . . ?
F3 C6 C7 C8 69.9(4) . . . . ?
F4 C6 C7 F5 73.5(4) . . . . ?
F4 C6 C7 F6 -167.6(4) . . . . ?
F4 C6 C7 C8 -47.5(5) . . . . ?
F5 C7 C8 F7 -177.4(5) . . . . ?
F5 C7 C8 F8 -55.6(6) . . . . ?
F5 C7 C8 F9 63.3(5) . . . . ?
F6 C7 C8 F7 67.0(5) . . . . ?
F6 C7 C8 F8 -171.2(5) . . . . ?
F6 C7 C8 F9 -52.4(6) . . . . ?
O1 C2 C3 C4 22.3(5) . . . . ?
O2 C4 C5 F1 62.1(3) . . . . ?
O2 C4 C5 F2 178.8(3) . . . . ?
O2 C4 C5 C6 -59.9(3) . . . . ?
C1 C2 C3 C4 -159.6(3) . . . . ?
C2 C3 C4 O2 77.2(4) . . . . ?
C2 C3 C4 C5 -163.3(3) . . . . ?
C3 C4 C5 F1 -58.5(3) . . . . ?
C3 C4 C5 F2 58.1(3) . . . . ?
C3 C4 C5 C6 179.4(3) . . . . ?
C4 C5 C6 F3 -40.9(4) . . . . ?
C4 C5 C6 F4 77.9(3) . . . . ?
C4 C5 C6 C7 -161.3(3) . . . . ?
C5 C6 C7 F5 -48.3(4) . . . . ?
C5 C6 C7 F6 70.7(4) . . . . ?
C5 C6 C7 C8 -169.3(3) . . . . ?
C6 C7 C8 F7 -54.9(6) . . . . ?
C6 C7 C8 F8 66.9(6) . . . . ?
C6 C7 C8 F9 -174.3(4) . . . . ?
C9 C1 C2 O1 9.5(6) . . . . ?
C9 C1 C2 C3 -168.5(4) . . . . ?
C10 C1 C2 O1 131.8(4) . . . . ?
C10 C1 C2 C3 -46.2(4) . . . . ?
C11 C1 C2 O1 -108.6(4) . . . . ?
C11 C1 C2 C3 73.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.432
_oxdiff_exptl_absorpt_empirical_full_min 0.338
####################################################################### 
# 
# 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_cs641
_database_code_depnum_ccdc_archive 'CCDC 1939261'
loop_
_audit_author_name
_audit_author_address
'Michel Giorgi'
;Aix Marseille universite
France
;
_audit_update_record             
;
2019-07-08 deposited with the CCDC.	2019-12-17 downloaded from the CCDC.
;
_audit_creation_date             2018-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 F6 O3'
_chemical_formula_sum            'C7 H10 F6 O3'
_chemical_formula_weight         256.15
_chemical_absolute_configuration ad
_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 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.90290(10)
_cell_length_b                   9.8824(2)
_cell_length_c                   10.7838(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.543(3)
_cell_angle_gamma                90
_cell_volume                     513.68(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.1620
_cell_measurement_theta_min      4.1590
_shelx_estimated_absorpt_T_max   0.901
_shelx_estimated_absorpt_T_min   0.539
_exptl_absorpt_coefficient_mu    1.766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7133
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.257
_diffrn_reflns_theta_min         4.170
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00 105.00   1.00    1.00    --    0.00  77.00-180.00  151
  2  ω   -100.00  51.00   1.00    1.00    --  -53.50  77.00 -60.00  151
  3  ω   -100.00  51.00   1.00    1.00    --  -53.50  77.00  60.00  151
  4  ω      7.00 158.00   1.00    1.00    --   53.50  77.00 150.00  151
  5  ω      7.00 158.00   1.00    1.00    --   53.50  77.00 -30.00  151
  6  ω      7.00 158.00   1.00    1.00    --   53.50  77.00 -90.00  151
  7  ω     61.00 178.00   1.00    8.00    --  107.00  77.00   0.00  117
  8  ω     61.00 178.00   1.00    8.00    --  107.00  77.00 -30.00  117
  9  ω     61.00 178.00   1.00    8.00    --  107.00  77.00-120.00  117
 10  ω     61.00 178.00   1.00    8.00    --  107.00  77.00 -90.00  117
 11  ω     61.00 178.00   1.00    8.00    --  107.00  77.00-150.00  117
 12  ω     61.00 178.00   1.00    8.00    --  107.00  77.00 120.00  117
 13  ω     61.00 178.00   1.00    8.00    --  107.00  77.00 -60.00  117
 14  ω     61.00 178.00   1.00    8.00    --  107.00  77.00 150.00  117
 15  ω     61.00 178.00   1.00    8.00    --  107.00  77.00  90.00  117
 16  ω     61.00 178.00   1.00    8.00    --  107.00  77.00-180.00  117
 17  ω     55.00 103.00   1.00    1.00    --    0.00-178.00  60.00   48
 18  ω   -152.00 -79.00   1.00    1.00    --  -53.50 -99.00  90.00   73
 19  ω   -151.00  -8.00   1.00    1.00    --  -53.50 -57.00  30.00  143
 20  ω      7.00 158.00   1.00    1.00    --   53.50  77.00-150.00  151
 21  ω      7.00 158.00   1.00    1.00    --   53.50  77.00  60.00  151
 22  ω     23.00 118.00   1.00    1.00    --   53.50-125.00-180.00   95
 23  ω     12.00 113.00   1.00    8.00    --  107.00-111.00 -60.00  101
 24  ω    100.00 178.00   1.00    8.00    --  107.00 111.00  90.00   78
 25  ω      7.00 157.00   1.00    8.00    --  107.00 -91.00  30.00  150
 26  ω     61.00 178.00   1.00    8.00    --  107.00  77.00  30.00  117
 27  ω     57.00 150.00   1.00    8.00    --  107.00 178.00-180.00   93
 28  ω     57.00 150.00   1.00    8.00    --  107.00 178.00 -60.00   93
 29  ω     61.00 178.00   1.00    8.00    --  107.00  77.00  60.00  117
 30  ω     62.00 178.00   1.00    8.00    --  107.00  63.00  60.00  116
 31  ω   -103.00 -34.00   1.00    1.00    --    0.00 178.00  30.00   69
 32  ω   -158.00 -21.00   1.00    1.00    --  -53.50 -77.00 -90.00  137
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1916832000
_diffrn_orient_matrix_UB_12      0.1168562000
_diffrn_orient_matrix_UB_13      -0.0557093000
_diffrn_orient_matrix_UB_21      -0.1640575000
_diffrn_orient_matrix_UB_22      -0.0149434000
_diffrn_orient_matrix_UB_23      0.1081632000
_diffrn_orient_matrix_UB_31      0.1960996000
_diffrn_orient_matrix_UB_32      0.1020774000
_diffrn_orient_matrix_UB_33      0.0795536000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.868
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                1815
_reflns_number_total             1855
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         1855
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.080
_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)+(0.0498P)²+0.0759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3)
;
_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
F1 F 0.1980(6) 0.9326(2) 0.0730(2) 0.0877(8) Uani 1 1 d . . . . .
F2 F 0.5097(6) 0.9241(3) 0.2401(3) 0.1033(9) Uani 1 1 d . . . . .
F3 F 0.1157(6) 0.8393(3) 0.2391(3) 0.0917(8) Uani 1 1 d . . . . .
F4 F 0.8345(5) 0.2034(3) 0.50207(19) 0.0856(7) Uani 1 1 d . . . . .
F5 F 1.2137(5) 0.2551(3) 0.4462(2) 0.0844(7) Uani 1 1 d . . . . .
F6 F 1.0164(6) 0.0683(2) 0.3865(2) 0.0911(8) Uani 1 1 d . . . . .
O1 O 0.1840(5) 0.6548(2) 0.05064(19) 0.0585(5) Uani 1 1 d . . . . .
H1 H 0.161787 0.684923 -0.021362 0.088 Uiso 1 1 calc GR . . . .
O2 O 0.3672(4) 0.4147(2) 0.14555(19) 0.0520(5) Uani 1 1 d . . . . .
H2 H 0.272365 0.459895 0.090006 0.078 Uiso 1 1 calc GR . . . .
O3 O 0.9572(4) 0.2495(2) 0.19059(16) 0.0493(5) Uani 1 1 d . . . . .
H3 H 1.089096 0.301888 0.200032 0.074 Uiso 1 1 calc GR . . . .
C1 C 0.3103(7) 0.8553(3) 0.1698(3) 0.0547(7) Uani 1 1 d . . . . .
C2 C 0.4106(6) 0.7213(3) 0.1265(2) 0.0452(6) Uani 1 1 d . . . . .
H2A H 0.556452 0.737480 0.077114 0.054 Uiso 1 1 calc R . . . .
C3 C 0.5228(6) 0.6322(3) 0.2389(3) 0.0462(6) Uani 1 1 d . . . . .
H3A H 0.382393 0.623473 0.291167 0.055 Uiso 1 1 calc R . . . .
H3B H 0.682952 0.676036 0.288969 0.055 Uiso 1 1 calc R . . . .
C4 C 0.6065(5) 0.4912(3) 0.2020(3) 0.0420(5) Uani 1 1 d . . . . .
H4 H 0.732334 0.499659 0.141488 0.050 Uiso 1 1 calc R . . . .
C5 C 0.7524(6) 0.4143(3) 0.3173(2) 0.0455(6) Uani 1 1 d . . . . .
H5A H 0.638721 0.417772 0.381974 0.055 Uiso 1 1 calc R . . . .
H5B H 0.926908 0.458897 0.350258 0.055 Uiso 1 1 calc R . . . .
C6 C 0.8097(6) 0.2667(3) 0.2897(2) 0.0433(6) Uani 1 1 d . . . . .
H6 H 0.630571 0.220757 0.265843 0.052 Uiso 1 1 calc R . . . .
C7 C 0.9680(7) 0.1972(3) 0.4063(3) 0.0542(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
F1 C1 1.329(4) . ?
F2 C1 1.312(4) . ?
F3 C1 1.325(4) . ?
F4 C7 1.321(4) . ?
F5 C7 1.332(4) . ?
F6 C7 1.321(4) . ?
O1 H1 0.8200 . ?
O1 C2 1.415(4) . ?
O2 H2 0.8200 . ?
O2 C4 1.435(3) . ?
O3 H3 0.8200 . ?
O3 C6 1.406(3) . ?
C1 C2 1.516(4) . ?
C2 H2A 0.9800 . ?
C2 C3 1.517(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.526(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.520(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.526(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.516(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
C2 O1 H1 109.5 . . ?
C4 O2 H2 109.5 . . ?
C6 O3 H3 109.5 . . ?
F1 C1 C2 111.8(3) . . ?
F2 C1 F1 108.3(3) . . ?
F2 C1 F3 105.9(3) . . ?
F2 C1 C2 112.4(3) . . ?
F3 C1 F1 105.9(3) . . ?
F3 C1 C2 112.1(3) . . ?
O1 C2 C1 108.6(2) . . ?
O1 C2 H2A 109.6 . . ?
O1 C2 C3 108.9(2) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 C3 110.6(2) . . ?
C3 C2 H2A 109.6 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C2 C3 C4 113.4(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
O2 C4 C3 110.7(2) . . ?
O2 C4 H4 109.1 . . ?
O2 C4 C5 108.0(2) . . ?
C3 C4 H4 109.1 . . ?
C5 C4 C3 110.6(2) . . ?
C5 C4 H4 109.1 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C4 C5 C6 113.2(2) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
O3 C6 C5 113.7(2) . . ?
O3 C6 H6 107.8 . . ?
O3 C6 C7 108.6(2) . . ?
C5 C6 H6 107.8 . . ?
C7 C6 C5 110.8(2) . . ?
C7 C6 H6 107.8 . . ?
F4 C7 F5 106.0(3) . . ?
F4 C7 C6 112.1(2) . . ?
F5 C7 C6 111.7(3) . . ?
F6 C7 F4 107.5(3) . . ?
F6 C7 F5 106.7(3) . . ?
F6 C7 C6 112.5(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
F1 C1 C2 O1 -57.4(3) . . . . ?
F1 C1 C2 C3 -176.8(3) . . . . ?
F2 C1 C2 O1 -179.4(3) . . . . ?
F2 C1 C2 C3 61.1(4) . . . . ?
F3 C1 C2 O1 61.5(3) . . . . ?
F3 C1 C2 C3 -58.0(3) . . . . ?
O1 C2 C3 C4 56.2(3) . . . . ?
O2 C4 C5 C6 51.5(3) . . . . ?
O3 C6 C7 F4 -176.9(3) . . . . ?
O3 C6 C7 F5 64.3(3) . . . . ?
O3 C6 C7 F6 -55.7(3) . . . . ?
C1 C2 C3 C4 175.5(2) . . . . ?
C2 C3 C4 O2 -67.9(3) . . . . ?
C2 C3 C4 C5 172.3(2) . . . . ?
C3 C4 C5 C6 172.8(2) . . . . ?
C4 C5 C6 O3 54.4(3) . . . . ?
C4 C5 C6 C7 177.1(2) . . . . ?
C5 C6 C7 F4 57.5(3) . . . . ?
C5 C6 C7 F5 -61.3(3) . . . . ?
C5 C6 C7 F6 178.7(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.725
_oxdiff_exptl_absorpt_empirical_full_min 0.548
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
