# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_pnna
_database_code_depnum_ccdc_archive 'CCDC 1839041'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 F13 O, C4 H12 N'
_chemical_formula_sum            'C11 H12 F13 N O'
_chemical_formula_weight         421.22
_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'
N N 0.0061 0.0033 '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           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   14.4972(6)
_cell_length_b                   14.7800(5)
_cell_length_c                   28.496(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6105.8(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    500
_cell_measurement_temperature    100
_cell_measurement_theta_max      20
_cell_measurement_theta_min      2
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.224
_exptl_absorpt_correction_T_max  0.9876
_exptl_absorpt_correction_T_min  0.8765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'd*Trek version 9.9.8.4'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.833
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3360
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1074
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            95237
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.105
_diffrn_ambient_temperature      100
_diffrn_detector                 'Image Plate'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4442
_reflns_number_total             6993
_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       ?
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        ?
_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, 2015)'
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     479
_refine_ls_number_reflns         6993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0847
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.052
_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)+(0.0553P)²+0.9209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1191
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
O1 O 0.39575(11) 0.11507(11) 0.37351(5) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.61710(11) 0.62522(10) 0.37905(5) 0.0275(4) Uani 1 1 d . . . . .
C1 C 0.48164(15) 0.14622(15) 0.37509(8) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.50075(16) 0.21311(16) 0.33364(8) 0.0257(5) Uani 1 1 d . . . . .
C3 C 0.43642(16) 0.29640(16) 0.33471(8) 0.0268(5) Uani 1 1 d . . . . .
C4 C 0.44187(16) 0.34723(16) 0.38140(8) 0.0249(5) Uani 1 1 d . . . . .
C5 C 0.43751(15) 0.28591(16) 0.42494(8) 0.0249(5) Uani 1 1 d . . . . .
C6 C 0.49771(15) 0.20028(15) 0.42146(8) 0.0238(5) Uani 1 1 d . . . . .
C7 C 0.55186(17) 0.06672(17) 0.37221(8) 0.0302(6) Uani 1 1 d . . . . .
C8 C 0.58568(16) 0.70875(15) 0.37270(7) 0.0229(5) Uani 1 1 d . . . . .
C9 C 0.52875(16) 0.74088(15) 0.41632(8) 0.0256(5) Uani 1 1 d . . . . .
C10 C 0.44408(17) 0.68106(16) 0.42592(8) 0.0291(5) Uani 1 1 d . . . . .
C11 C 0.38022(17) 0.67357(17) 0.38308(9) 0.0317(6) Uani 1 1 d . . . . .
C12 C 0.43106(17) 0.65390(17) 0.33692(9) 0.0306(6) Uani 1 1 d . . . . .
C13 C 0.51786(16) 0.71205(16) 0.32968(8) 0.0263(5) Uani 1 1 d . . . . .
C14 C 0.66663(17) 0.77534(15) 0.36449(8) 0.0264(5) Uani 1 1 d . . . . .
N1 N 0.250000 0.000000 0.48443(9) 0.0288(6) Uani 1 2 d S T P . .
C16 C 0.3265(2) -0.0335(2) 0.45418(10) 0.0474(7) Uani 1 1 d . . . . .
H16A H 0.348281 0.015724 0.433981 0.071 Uiso 1 1 calc GR . . . .
H16B H 0.304176 -0.083526 0.434680 0.071 Uiso 1 1 calc GR . . . .
H16C H 0.377346 -0.054718 0.473986 0.071 Uiso 1 1 calc GR . . . .
C17 C 0.2844(2) 0.07557(19) 0.51475(9) 0.0433(7) Uani 1 1 d . . . . .
H17A H 0.234137 0.097317 0.534796 0.065 Uiso 1 1 calc GR . . . .
H17B H 0.306409 0.125193 0.494884 0.065 Uiso 1 1 calc GR . . . .
H17C H 0.335146 0.053646 0.534419 0.065 Uiso 1 1 calc GR . . . .
N2 N 0.250000 0.500000 0.20874(9) 0.0240(6) Uani 1 2 d S T P . .
C19 C 0.29887(17) 0.56697(17) 0.17812(8) 0.0328(6) Uani 1 1 d . . . . .
H19A H 0.253666 0.599423 0.158867 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.342419 0.535081 0.157669 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.332491 0.610235 0.197781 0.049 Uiso 1 1 calc GR . . . .
C20 C 0.31829(18) 0.45179(18) 0.23843(9) 0.0348(6) Uani 1 1 d . . . . .
H20A H 0.351213 0.495586 0.258080 0.052 Uiso 1 1 calc GR . . . .
H20B H 0.362458 0.419910 0.218323 0.052 Uiso 1 1 calc GR . . . .
H20C H 0.286269 0.408034 0.258492 0.052 Uiso 1 1 calc GR . . . .
N3 N 0.250000 0.500000 0.53481(9) 0.0233(6) Uani 1 2 d S T P . .
C22 C 0.18969(17) 0.44363(17) 0.56534(8) 0.0326(6) Uani 1 1 d . . . . .
H22A H 0.149791 0.483044 0.584128 0.049 Uiso 1 1 calc GR . . . .
H22B H 0.228025 0.406763 0.586240 0.049 Uiso 1 1 calc GR . . . .
H22C H 0.151548 0.403982 0.545767 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.30841(18) 0.44053(18) 0.50501(9) 0.0376(6) Uani 1 1 d . . . . .
H23A H 0.268863 0.402505 0.485286 0.056 Uiso 1 1 calc GR . . . .
H23B H 0.346761 0.402001 0.525076 0.056 Uiso 1 1 calc GR . . . .
H23C H 0.348109 0.477882 0.485020 0.056 Uiso 1 1 calc GR . . . .
N4 N 0.750000 0.500000 0.27137(9) 0.0264(6) Uani 1 2 d S T P . .
C25 C 0.6699(2) 0.47448(18) 0.30161(10) 0.0428(7) Uani 1 1 d . . . . .
H25A H 0.616607 0.460486 0.281760 0.064 Uiso 1 1 calc GR . . . .
H25B H 0.654693 0.524974 0.322500 0.064 Uiso 1 1 calc GR . . . .
H25C H 0.686003 0.421224 0.320397 0.064 Uiso 1 1 calc GR . . . .
C26 C 0.72467(18) 0.57838(17) 0.24099(8) 0.0344(6) Uani 1 1 d . . . . .
H26A H 0.776868 0.593778 0.220648 0.052 Uiso 1 1 calc GR . . . .
H26B H 0.709249 0.630512 0.260742 0.052 Uiso 1 1 calc GR . . . .
H26C H 0.671250 0.562346 0.221625 0.052 Uiso 1 1 calc GR . . . .
F1 F 0.58832(9) 0.24633(9) 0.33283(5) 0.0306(3) Uani 1 1 d . . . . .
F2 F 0.48799(10) 0.17156(10) 0.29196(5) 0.0365(4) Uani 1 1 d . . . . .
F3 F 0.46268(10) 0.35525(9) 0.30041(5) 0.0342(3) Uani 1 1 d . . . . .
F4 F 0.34856(9) 0.27350(9) 0.32563(5) 0.0337(3) Uani 1 1 d . . . . .
F5 F 0.52263(9) 0.39227(9) 0.38248(4) 0.0291(3) Uani 1 1 d . . . . .
F6 F 0.37357(10) 0.40892(9) 0.38394(5) 0.0346(3) Uani 1 1 d . . . . .
F7 F 0.46636(10) 0.33662(9) 0.46195(4) 0.0315(3) Uani 1 1 d . . . . .
F8 F 0.34905(9) 0.26367(9) 0.43329(5) 0.0305(3) Uani 1 1 d . . . . .
F9 F 0.58699(9) 0.22719(9) 0.42792(4) 0.0284(3) Uani 1 1 d . . . . .
F10 F 0.47651(10) 0.14803(9) 0.45938(5) 0.0313(3) Uani 1 1 d . . . . .
F11 F 0.64122(10) 0.08910(10) 0.37036(5) 0.0384(4) Uani 1 1 d . . . . .
F12 F 0.54244(10) 0.01156(9) 0.40938(5) 0.0402(4) Uani 1 1 d . . . . .
F13 F 0.53519(11) 0.01582(10) 0.33401(5) 0.0424(4) Uani 1 1 d . . . . .
F14 F 0.58315(10) 0.73926(9) 0.45499(5) 0.0334(3) Uani 1 1 d . . . . .
F15 F 0.49648(10) 0.82724(9) 0.41277(5) 0.0324(3) Uani 1 1 d . . . . .
F16 F 0.46898(9) 0.59743(9) 0.43996(5) 0.0347(3) Uani 1 1 d . . . . .
F17 F 0.39451(10) 0.71764(10) 0.46181(5) 0.0400(4) Uani 1 1 d . . . . .
F18 F 0.31709(10) 0.60829(10) 0.39114(6) 0.0428(4) Uani 1 1 d . . . . .
F19 F 0.33505(10) 0.75284(10) 0.37842(5) 0.0384(4) Uani 1 1 d . . . . .
F20 F 0.45230(10) 0.56520(9) 0.33517(5) 0.0368(4) Uani 1 1 d . . . . .
F21 F 0.37116(10) 0.66986(10) 0.30113(5) 0.0416(4) Uani 1 1 d . . . . .
F22 F 0.56007(10) 0.67953(10) 0.29065(4) 0.0348(3) Uani 1 1 d . . . . .
F23 F 0.48903(10) 0.79729(9) 0.31881(5) 0.0327(3) Uani 1 1 d . . . . .
F24 F 0.72796(9) 0.76874(9) 0.39957(5) 0.0359(4) Uani 1 1 d . . . . .
F25 F 0.64495(10) 0.86341(9) 0.36110(5) 0.0346(3) Uani 1 1 d . . . . .
F26 F 0.71272(10) 0.75438(9) 0.32496(5) 0.0350(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.328(3) . ?
O2 C8 1.328(3) . ?
C1 C2 1.565(3) . ?
C1 C6 1.561(3) . ?
C1 C7 1.557(3) . ?
C2 C3 1.545(3) . ?
C2 F1 1.361(3) . ?
C2 F2 1.350(3) . ?
C3 C4 1.530(3) . ?
C3 F3 1.363(3) . ?
C3 F4 1.343(3) . ?
C4 C5 1.538(3) . ?
C4 F5 1.347(3) . ?
C4 F6 1.348(3) . ?
C5 C6 1.540(3) . ?
C5 F7 1.360(3) . ?
C5 F8 1.345(3) . ?
C6 F9 1.367(2) . ?
C6 F10 1.363(3) . ?
C7 F11 1.338(3) . ?
C7 F12 1.343(3) . ?
C7 F13 1.345(3) . ?
C8 C9 1.566(3) . ?
C8 C13 1.572(3) . ?
C8 C14 1.549(3) . ?
C9 C10 1.537(3) . ?
C9 F14 1.355(3) . ?
C9 F15 1.363(3) . ?
C10 C11 1.536(3) . ?
C10 F16 1.348(3) . ?
C10 F17 1.362(3) . ?
C11 C12 1.536(3) . ?
C11 F18 1.350(3) . ?
C11 F19 1.349(3) . ?
C12 C13 1.538(3) . ?
C12 F20 1.348(3) . ?
C12 F21 1.360(3) . ?
C13 F22 1.357(3) . ?
C13 F23 1.363(3) . ?
C14 F24 1.342(3) . ?
C14 F25 1.343(3) . ?
C14 F26 1.346(3) . ?
N1 C16 1.489(3) 2 ?
N1 C16 1.489(3) . ?
N1 C17 1.497(3) . ?
N1 C17 1.498(3) 2 ?
N2 C19 1.498(3) 2_565 ?
N2 C19 1.498(3) . ?
N2 C20 1.485(3) 2_565 ?
N2 C20 1.484(3) . ?
N3 C22 1.489(3) . ?
N3 C22 1.489(3) 2_565 ?
N3 C23 1.487(3) . ?
N3 C23 1.487(3) 2_565 ?
N4 C25 1.494(3) 2_665 ?
N4 C25 1.494(3) . ?
N4 C26 1.492(3) . ?
N4 C26 1.492(3) 2_665 ?

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
O1 C1 C2 111.06(18) . . ?
O1 C1 C6 110.24(18) . . ?
O1 C1 C7 110.46(19) . . ?
C6 C1 C2 106.80(18) . . ?
C7 C1 C2 108.73(18) . . ?
C7 C1 C6 109.47(18) . . ?
C3 C2 C1 112.43(19) . . ?
F1 C2 C1 113.93(18) . . ?
F1 C2 C3 106.01(18) . . ?
F2 C2 C1 110.64(18) . . ?
F2 C2 C3 107.29(18) . . ?
F2 C2 F1 106.09(18) . . ?
C4 C3 C2 112.17(18) . . ?
F3 C3 C2 109.02(19) . . ?
F3 C3 C4 107.21(19) . . ?
F4 C3 C2 111.59(19) . . ?
F4 C3 C4 109.89(19) . . ?
F4 C3 F3 106.72(18) . . ?
C3 C4 C5 114.21(19) . . ?
F5 C4 C3 107.90(18) . . ?
F5 C4 C5 107.97(18) . . ?
F5 C4 F6 107.63(18) . . ?
F6 C4 C3 109.92(18) . . ?
F6 C4 C5 108.99(18) . . ?
C4 C5 C6 114.14(18) . . ?
F7 C5 C4 106.75(18) . . ?
F7 C5 C6 109.18(18) . . ?
F8 C5 C4 109.02(18) . . ?
F8 C5 C6 110.53(18) . . ?
F8 C5 F7 106.91(17) . . ?
C5 C6 C1 112.97(18) . . ?
F9 C6 C1 113.85(18) . . ?
F9 C6 C5 106.79(18) . . ?
F10 C6 C1 110.32(18) . . ?
F10 C6 C5 106.66(18) . . ?
F10 C6 F9 105.75(17) . . ?
F11 C7 C1 116.7(2) . . ?
F11 C7 F12 106.23(19) . . ?
F11 C7 F13 106.28(19) . . ?
F12 C7 C1 110.48(19) . . ?
F12 C7 F13 106.3(2) . . ?
F13 C7 C1 110.32(19) . . ?
O2 C8 C9 110.75(18) . . ?
O2 C8 C13 110.46(18) . . ?
O2 C8 C14 110.56(19) . . ?
C9 C8 C13 106.26(18) . . ?
C14 C8 C9 109.05(18) . . ?
C14 C8 C13 109.66(18) . . ?
C10 C9 C8 112.82(19) . . ?
F14 C9 C8 109.48(18) . . ?
F14 C9 C10 108.05(18) . . ?
F14 C9 F15 106.06(18) . . ?
F15 C9 C8 113.95(18) . . ?
F15 C9 C10 106.12(18) . . ?
C11 C10 C9 112.41(19) . . ?
F16 C10 C9 111.48(19) . . ?
F16 C10 C11 109.3(2) . . ?
F16 C10 F17 106.40(18) . . ?
F17 C10 C9 109.07(19) . . ?
F17 C10 C11 107.91(19) . . ?
C12 C11 C10 113.9(2) . . ?
F18 C11 C10 109.0(2) . . ?
F18 C11 C12 109.6(2) . . ?
F19 C11 C10 108.0(2) . . ?
F19 C11 C12 108.2(2) . . ?
F19 C11 F18 107.97(19) . . ?
C11 C12 C13 113.7(2) . . ?
F20 C12 C11 109.0(2) . . ?
F20 C12 C13 110.6(2) . . ?
F20 C12 F21 106.67(19) . . ?
F21 C12 C11 107.6(2) . . ?
F21 C12 C13 109.0(2) . . ?
C12 C13 C8 112.95(18) . . ?
F22 C13 C8 110.23(18) . . ?
F22 C13 C12 106.32(19) . . ?
F22 C13 F23 106.22(17) . . ?
F23 C13 C8 113.43(19) . . ?
F23 C13 C12 107.23(18) . . ?
F24 C14 C8 110.08(18) . . ?
F24 C14 F25 106.21(18) . . ?
F24 C14 F26 106.14(19) . . ?
F25 C14 C8 116.71(19) . . ?
F25 C14 F26 106.21(18) . . ?
F26 C14 C8 110.87(18) . . ?
C16 N1 C16 109.3(3) 2 . ?
C16 N1 C17 109.51(16) . . ?
C16 N1 C17 109.51(16) . 2 ?
C16 N1 C17 109.51(16) 2 2 ?
C16 N1 C17 109.51(16) 2 . ?
C17 N1 C17 109.5(3) . 2 ?
C19 N2 C19 108.7(2) . 2_565 ?
C20 N2 C19 109.50(14) 2_565 2_565 ?
C20 N2 C19 109.29(14) 2_565 . ?
C20 N2 C19 109.50(14) . . ?
C20 N2 C19 109.28(14) . 2_565 ?
C20 N2 C20 110.5(3) . 2_565 ?
C22 N3 C22 108.5(2) . 2_565 ?
C23 N3 C22 109.73(15) 2_565 2_565 ?
C23 N3 C22 109.28(15) . 2_565 ?
C23 N3 C22 109.28(15) 2_565 . ?
C23 N3 C22 109.73(15) . . ?
C23 N3 C23 110.3(3) 2_565 . ?
C25 N4 C25 109.5(3) . 2_665 ?
C26 N4 C25 109.84(15) 2_665 2_665 ?
C26 N4 C25 109.25(15) 2_665 . ?
C26 N4 C25 109.85(15) . . ?
C26 N4 C25 109.25(15) . 2_665 ?
C26 N4 C26 109.1(3) . 2_665 ?

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
O1 C1 C2 C3 60.4(2) . . . . ?
O1 C1 C2 F1 -178.96(17) . . . . ?
O1 C1 C2 F2 -59.5(2) . . . . ?
O1 C1 C6 C5 -64.0(2) . . . . ?
O1 C1 C6 F9 173.99(17) . . . . ?
O1 C1 C6 F10 55.3(2) . . . . ?
O1 C1 C7 F11 175.78(19) . . . . ?
O1 C1 C7 F12 -62.8(2) . . . . ?
O1 C1 C7 F13 54.4(3) . . . . ?
O2 C8 C9 C10 -60.7(2) . . . . ?
O2 C8 C9 F14 59.7(2) . . . . ?
O2 C8 C9 F15 178.25(18) . . . . ?
O2 C8 C13 C12 62.9(2) . . . . ?
O2 C8 C13 F22 -55.9(2) . . . . ?
O2 C8 C13 F23 -174.85(18) . . . . ?
O2 C8 C14 F24 -54.0(2) . . . . ?
O2 C8 C14 F25 -175.11(18) . . . . ?
O2 C8 C14 F26 63.1(2) . . . . ?
C1 C2 C3 C4 55.8(2) . . . . ?
C1 C2 C3 F3 174.38(17) . . . . ?
C1 C2 C3 F4 -68.0(2) . . . . ?
C2 C1 C6 C5 56.8(2) . . . . ?
C2 C1 C6 F9 -65.3(2) . . . . ?
C2 C1 C6 F10 176.05(17) . . . . ?
C2 C1 C7 F11 53.7(3) . . . . ?
C2 C1 C7 F12 175.11(18) . . . . ?
C2 C1 C7 F13 -67.7(2) . . . . ?
C2 C3 C4 C5 -46.3(3) . . . . ?
C2 C3 C4 F5 73.8(2) . . . . ?
C2 C3 C4 F6 -169.13(18) . . . . ?
C3 C4 C5 C6 44.1(3) . . . . ?
C3 C4 C5 F7 164.81(18) . . . . ?
C3 C4 C5 F8 -80.0(2) . . . . ?
C4 C5 C6 C1 -50.5(3) . . . . ?
C4 C5 C6 F9 75.4(2) . . . . ?
C4 C5 C6 F10 -171.85(18) . . . . ?
C6 C1 C2 C3 -59.8(2) . . . . ?
C6 C1 C2 F1 60.8(2) . . . . ?
C6 C1 C2 F2 -179.77(17) . . . . ?
C6 C1 C7 F11 -62.7(3) . . . . ?
C6 C1 C7 F12 58.8(2) . . . . ?
C6 C1 C7 F13 175.99(18) . . . . ?
C7 C1 C2 C3 -177.86(18) . . . . ?
C7 C1 C2 F1 -57.2(2) . . . . ?
C7 C1 C2 F2 62.2(2) . . . . ?
C7 C1 C6 C5 174.33(18) . . . . ?
C7 C1 C6 F9 52.3(2) . . . . ?
C7 C1 C6 F10 -66.4(2) . . . . ?
C8 C9 C10 C11 -55.5(2) . . . . ?
C8 C9 C10 F16 67.7(2) . . . . ?
C8 C9 C10 F17 -175.10(17) . . . . ?
C9 C8 C13 C12 -57.3(2) . . . . ?
C9 C8 C13 F22 -176.08(18) . . . . ?
C9 C8 C13 F23 65.0(2) . . . . ?
C9 C8 C14 F24 68.0(2) . . . . ?
C9 C8 C14 F25 -53.1(3) . . . . ?
C9 C8 C14 F26 -174.85(17) . . . . ?
C9 C10 C11 C12 46.5(3) . . . . ?
C9 C10 C11 F18 169.28(19) . . . . ?
C9 C10 C11 F19 -73.7(2) . . . . ?
C10 C11 C12 C13 -45.2(3) . . . . ?
C10 C11 C12 F20 78.7(2) . . . . ?
C10 C11 C12 F21 -166.02(19) . . . . ?
C11 C12 C13 C8 52.1(3) . . . . ?
C11 C12 C13 F22 173.07(18) . . . . ?
C11 C12 C13 F23 -73.6(2) . . . . ?
C13 C8 C9 C10 59.3(2) . . . . ?
C13 C8 C9 F14 179.68(17) . . . . ?
C13 C8 C9 F15 -61.8(2) . . . . ?
C13 C8 C14 F24 -176.02(17) . . . . ?
C13 C8 C14 F25 62.9(2) . . . . ?
C13 C8 C14 F26 -58.9(2) . . . . ?
C14 C8 C9 C10 177.45(19) . . . . ?
C14 C8 C9 F14 -62.2(2) . . . . ?
C14 C8 C9 F15 56.4(2) . . . . ?
C14 C8 C13 C12 -175.03(19) . . . . ?
C14 C8 C13 F22 66.2(2) . . . . ?
C14 C8 C13 F23 -52.8(2) . . . . ?
F1 C2 C3 C4 -69.3(2) . . . . ?
F1 C2 C3 F3 49.3(2) . . . . ?
F1 C2 C3 F4 166.91(17) . . . . ?
F2 C2 C3 C4 177.67(18) . . . . ?
F2 C2 C3 F3 -63.8(2) . . . . ?
F2 C2 C3 F4 53.9(2) . . . . ?
F3 C3 C4 C5 -165.93(18) . . . . ?
F3 C3 C4 F5 -45.9(2) . . . . ?
F3 C3 C4 F6 71.2(2) . . . . ?
F4 C3 C4 C5 78.5(2) . . . . ?
F4 C3 C4 F5 -161.49(17) . . . . ?
F4 C3 C4 F6 -44.4(2) . . . . ?
F5 C4 C5 C6 -75.9(2) . . . . ?
F5 C4 C5 F7 44.8(2) . . . . ?
F5 C4 C5 F8 159.95(17) . . . . ?
F6 C4 C5 C6 167.44(18) . . . . ?
F6 C4 C5 F7 -71.8(2) . . . . ?
F6 C4 C5 F8 43.3(2) . . . . ?
F7 C5 C6 C1 -169.85(17) . . . . ?
F7 C5 C6 F9 -43.9(2) . . . . ?
F7 C5 C6 F10 68.8(2) . . . . ?
F8 C5 C6 C1 72.8(2) . . . . ?
F8 C5 C6 F9 -161.26(17) . . . . ?
F8 C5 C6 F10 -48.5(2) . . . . ?
F14 C9 C10 C11 -176.64(19) . . . . ?
F14 C9 C10 F16 -53.5(2) . . . . ?
F14 C9 C10 F17 63.7(2) . . . . ?
F15 C9 C10 C11 70.0(2) . . . . ?
F15 C9 C10 F16 -166.86(18) . . . . ?
F15 C9 C10 F17 -49.7(2) . . . . ?
F16 C10 C11 C12 -77.8(2) . . . . ?
F16 C10 C11 F18 44.9(2) . . . . ?
F16 C10 C11 F19 161.94(18) . . . . ?
F17 C10 C11 C12 166.85(19) . . . . ?
F17 C10 C11 F18 -70.4(2) . . . . ?
F17 C10 C11 F19 46.6(2) . . . . ?
F18 C11 C12 C13 -167.60(19) . . . . ?
F18 C11 C12 F20 -43.7(3) . . . . ?
F18 C11 C12 F21 71.6(2) . . . . ?
F19 C11 C12 C13 74.9(2) . . . . ?
F19 C11 C12 F20 -161.27(18) . . . . ?
F19 C11 C12 F21 -45.9(3) . . . . ?
F20 C12 C13 C8 -71.0(2) . . . . ?
F20 C12 C13 F22 50.1(2) . . . . ?
F20 C12 C13 F23 163.36(18) . . . . ?
F21 C12 C13 C8 172.10(18) . . . . ?
F21 C12 C13 F22 -66.9(2) . . . . ?
F21 C12 C13 F23 46.4(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_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_pca21_b
_database_code_depnum_ccdc_archive 'CCDC 1839049'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
# end Validation Reply Form
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H2 F10 O2'
_chemical_formula_sum            'C6 H2 F10 O2'
_chemical_formula_weight         296.08
_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 0.0033 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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.3768(4)
_cell_length_b                   20.2598(6)
_cell_length_c                   8.3401(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1753.35(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7976
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.442
_cell_measurement_theta_min      3.291
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0593 before and 0.0373 after correction. The Ratio of minimum to maximum transmission is 0.9572. 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    2.243
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.2
_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  0.0228
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18866
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_min         2.010
_diffrn_ambient_temperature      100.02
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3719
_reflns_number_total             4001
_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 V8.38A (Madison, 2016)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT V8.38A (Madison, 2016)'
_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, 2015)'
_refine_diff_density_max         0.454
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 1651 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.085
_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)+(0.0352P)²+0.4431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0685
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O1-H1 \\sim O2-H2 \\sim O3-H3 \\sim O4-H4
 with sigma of 0.02
3.a Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O1(H1), O2(H2), O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.35316(16) 0.44502(7) 0.8132(2) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.3698(2) 0.34695(11) 0.6635(3) 0.0111(5) Uani 1 1 d . . . . .
O1 O 0.38726(18) 0.32814(8) 0.5059(2) 0.0130(4) Uani 1 1 d D . . . .
H1 H 0.396(3) 0.2893(10) 0.5015(4) 0.020 Uiso 1 1 calc DGR . . . .
F2 F 0.32484(16) 0.45181(7) 0.5543(2) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.3947(3) 0.42231(11) 0.6696(3) 0.0125(6) Uani 1 1 d . . . . .
O2 O 0.2420(2) 0.33321(7) 0.7083(2) 0.0136(4) Uani 1 1 d D . . . .
H2 H 0.2298(9) 0.3460(12) 0.797(3) 0.020 Uiso 1 1 calc DGR . . . .
C6 C 0.4638(3) 0.30974(11) 0.7767(3) 0.0124(5) Uani 1 1 d . . . . .
F6 F 0.75087(19) 0.41693(7) 0.7220(2) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.6065(3) 0.32866(13) 0.7565(3) 0.0139(5) Uani 1 1 d . . . . .
F5 F 0.60793(17) 0.42469(7) 0.9133(2) 0.0200(4) Uani 1 1 d . . . . .
O4 O 0.32520(19) 0.20441(9) 0.1292(2) 0.0145(4) Uani 1 1 d D . . . .
H4 H 0.316(3) 0.2420(10) 0.149(2) 0.022 Uiso 1 1 calc DGR . . . .
F4 F 0.57329(17) 0.43138(8) 0.4970(2) 0.0200(4) Uani 1 1 d . . . . .
C4 C 0.6278(3) 0.40377(13) 0.7628(4) 0.0153(6) Uani 1 1 d . . . . .
O3 O 0.36610(18) 0.19758(8) 0.4032(2) 0.0127(4) Uani 1 1 d D . . . .
H3 H 0.299(2) 0.1830(11) 0.4293(15) 0.019 Uiso 1 1 calc DGR . . . .
F3 F 0.54883(16) 0.50724(7) 0.6799(2) 0.0225(4) Uani 1 1 d . . . . .
C3 C 0.5374(3) 0.44237(12) 0.6492(4) 0.0146(6) Uani 1 1 d . . . . .
F9 F 0.42876(16) 0.32117(7) 0.9297(2) 0.0159(4) Uani 1 1 d . . . . .
C9 C 0.4622(3) 0.05769(12) 0.3435(4) 0.0151(6) Uani 1 1 d . . . . .
F8 F 0.64842(17) 0.30568(8) 0.61520(19) 0.0187(4) Uani 1 1 d . . . . .
C8 C 0.3722(3) 0.09968(12) 0.2370(4) 0.0136(6) Uani 1 1 d . . . . .
F7 F 0.67518(17) 0.30031(8) 0.8739(2) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.3972(2) 0.17476(11) 0.2495(3) 0.0107(5) Uani 1 1 d . . . . .
F10 F 0.45162(16) 0.24425(6) 0.7484(2) 0.0171(4) Uani 1 1 d . . . . .
C10 C 0.6060(3) 0.07492(12) 0.3227(4) 0.0140(6) Uani 1 1 d . . . . .
F20 F 0.56016(15) 0.25560(6) 0.2588(2) 0.0174(4) Uani 1 1 d . . . . .
F19 F 0.57501(17) 0.18013(8) 0.0731(2) 0.0175(4) Uani 1 1 d . . . . .
F18 F 0.61927(16) 0.16893(7) 0.4871(2) 0.0180(4) Uani 1 1 d . . . . .
F17 F 0.75555(17) 0.16072(6) 0.2901(2) 0.0200(4) Uani 1 1 d . . . . .
F16 F 0.67441(17) 0.04350(7) 0.4345(2) 0.0228(4) Uani 1 1 d . . . . .
F15 F 0.64415(17) 0.05383(8) 0.1774(2) 0.0201(4) Uani 1 1 d . . . . .
F14 F 0.42911(17) 0.06719(7) 0.4975(2) 0.0195(4) Uani 1 1 d . . . . .
F13 F 0.44498(15) -0.00650(7) 0.3077(2) 0.0220(4) Uani 1 1 d . . . . .
F12 F 0.24933(18) 0.08821(6) 0.2806(2) 0.0195(3) Uani 1 1 d . . . . .
C12 C 0.5420(2) 0.19082(12) 0.2274(3) 0.0116(5) Uani 1 1 d . . . . .
F11 F 0.38677(17) 0.08027(8) 0.0836(2) 0.0189(4) Uani 1 1 d . . . . .
C11 C 0.6333(3) 0.14990(12) 0.3343(3) 0.0135(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C2 1.353(3) . ?
C1 O1 1.380(3) . ?
C1 C2 1.549(3) . ?
C1 O2 1.406(3) . ?
C1 C6 1.552(4) . ?
O1 H1 0.79(2) . ?
F2 C2 1.344(3) . ?
C2 C3 1.546(4) . ?
O2 H2 0.80(2) . ?
C6 C5 1.539(4) . ?
C6 F9 1.347(3) . ?
C6 F10 1.354(3) . ?
F6 C4 1.348(3) . ?
C5 C4 1.539(4) . ?
C5 F8 1.340(3) . ?
C5 F7 1.340(3) . ?
F5 C4 1.341(4) . ?
O4 H4 0.79(2) . ?
O4 C7 1.387(3) . ?
F4 C3 1.342(4) . ?
C4 C3 1.545(4) . ?
O3 H3 0.79(2) . ?
O3 C7 1.401(3) . ?
F3 C3 1.344(3) . ?
C9 C8 1.544(4) . ?
C9 C10 1.542(4) . ?
C9 F14 1.344(3) . ?
C9 F13 1.346(3) . ?
C8 C7 1.547(3) . ?
C8 F12 1.346(3) . ?
C8 F11 1.347(3) . ?
C7 C12 1.548(3) . ?
C10 F16 1.334(3) . ?
C10 F15 1.345(3) . ?
C10 C11 1.548(4) . ?
F20 C12 1.352(3) . ?
F19 C12 1.349(3) . ?
F18 C11 1.339(3) . ?
F17 C11 1.339(3) . ?
C12 C11 1.543(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
O1 C1 C2 106.3(2) . . ?
O1 C1 O2 108.8(2) . . ?
O1 C1 C6 111.2(2) . . ?
C2 C1 C6 110.7(2) . . ?
O2 C1 C2 110.10(19) . . ?
O2 C1 C6 109.5(2) . . ?
C1 O1 H1 109.5 . . ?
F1 C2 C1 108.1(2) . . ?
F1 C2 C3 108.2(2) . . ?
F2 C2 F1 108.09(19) . . ?
F2 C2 C1 109.0(2) . . ?
F2 C2 C3 108.7(2) . . ?
C3 C2 C1 114.5(2) . . ?
C1 O2 H2 109.5 . . ?
C5 C6 C1 114.7(2) . . ?
F9 C6 C1 108.9(2) . . ?
F9 C6 C5 108.7(2) . . ?
F9 C6 F10 108.0(2) . . ?
F10 C6 C1 108.2(2) . . ?
F10 C6 C5 108.3(2) . . ?
C4 C5 C6 112.4(2) . . ?
F8 C5 C6 108.8(2) . . ?
F8 C5 C4 109.1(2) . . ?
F8 C5 F7 108.7(2) . . ?
F7 C5 C6 109.0(2) . . ?
F7 C5 C4 108.8(2) . . ?
C7 O4 H4 109.5 . . ?
F6 C4 C5 108.9(2) . . ?
F6 C4 C3 108.7(2) . . ?
C5 C4 C3 113.1(2) . . ?
F5 C4 F6 108.6(2) . . ?
F5 C4 C5 108.8(2) . . ?
F5 C4 C3 108.7(2) . . ?
C7 O3 H3 109.5 . . ?
F4 C3 C2 109.0(2) . . ?
F4 C3 C4 109.1(2) . . ?
F4 C3 F3 108.5(2) . . ?
C4 C3 C2 112.4(2) . . ?
F3 C3 C2 108.7(2) . . ?
F3 C3 C4 109.0(2) . . ?
C10 C9 C8 113.3(2) . . ?
F14 C9 C8 108.4(2) . . ?
F14 C9 C10 108.8(3) . . ?
F14 C9 F13 108.4(2) . . ?
F13 C9 C8 108.9(2) . . ?
F13 C9 C10 108.8(2) . . ?
C9 C8 C7 113.7(2) . . ?
F12 C8 C9 108.8(2) . . ?
F12 C8 C7 108.1(2) . . ?
F12 C8 F11 108.2(2) . . ?
F11 C8 C9 108.5(2) . . ?
F11 C8 C7 109.4(2) . . ?
O4 C7 O3 113.26(19) . . ?
O4 C7 C8 106.7(2) . . ?
O4 C7 C12 110.2(2) . . ?
O3 C7 C8 110.3(2) . . ?
O3 C7 C12 105.2(2) . . ?
C8 C7 C12 111.20(19) . . ?
C9 C10 C11 113.1(2) . . ?
F16 C10 C9 109.2(2) . . ?
F16 C10 F15 108.8(2) . . ?
F16 C10 C11 109.1(2) . . ?
F15 C10 C9 108.3(2) . . ?
F15 C10 C11 108.3(2) . . ?
F20 C12 C7 108.47(19) . . ?
F20 C12 C11 108.9(2) . . ?
F19 C12 C7 109.0(2) . . ?
F19 C12 F20 107.8(2) . . ?
F19 C12 C11 108.0(2) . . ?
C11 C12 C7 114.5(2) . . ?
F18 C11 C10 108.8(2) . . ?
F18 C11 C12 109.1(2) . . ?
F17 C11 C10 108.5(2) . . ?
F17 C11 F18 108.6(2) . . ?
F17 C11 C12 109.6(2) . . ?
C12 C11 C10 112.2(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
F1 C2 C3 F4 -168.58(19) . . . . ?
F1 C2 C3 C4 70.3(3) . . . . ?
F1 C2 C3 F3 -50.4(3) . . . . ?
C1 C2 C3 F4 70.8(3) . . . . ?
C1 C2 C3 C4 -50.4(3) . . . . ?
C1 C2 C3 F3 -171.1(2) . . . . ?
C1 C6 C5 C4 51.1(3) . . . . ?
C1 C6 C5 F8 -69.8(3) . . . . ?
C1 C6 C5 F7 171.8(2) . . . . ?
O1 C1 C2 F1 167.6(2) . . . . ?
O1 C1 C2 F2 50.4(3) . . . . ?
O1 C1 C2 C3 -71.7(3) . . . . ?
O1 C1 C6 C5 68.3(3) . . . . ?
O1 C1 C6 F9 -169.73(19) . . . . ?
O1 C1 C6 F10 -52.7(3) . . . . ?
F2 C2 C3 F4 -51.4(3) . . . . ?
F2 C2 C3 C4 -172.5(2) . . . . ?
F2 C2 C3 F3 66.7(3) . . . . ?
C2 C1 C6 C5 -49.7(3) . . . . ?
C2 C1 C6 F9 72.2(3) . . . . ?
C2 C1 C6 F10 -170.7(2) . . . . ?
O2 C1 C2 F1 49.9(3) . . . . ?
O2 C1 C2 F2 -67.4(3) . . . . ?
O2 C1 C2 C3 170.6(2) . . . . ?
O2 C1 C6 C5 -171.3(2) . . . . ?
O2 C1 C6 F9 -49.4(3) . . . . ?
O2 C1 C6 F10 67.7(3) . . . . ?
C6 C1 C2 F1 -71.4(3) . . . . ?
C6 C1 C2 F2 171.3(2) . . . . ?
C6 C1 C2 C3 49.3(3) . . . . ?
C6 C5 C4 F6 -171.4(2) . . . . ?
C6 C5 C4 F5 70.4(3) . . . . ?
C6 C5 C4 C3 -50.5(3) . . . . ?
F6 C4 C3 C2 171.2(2) . . . . ?
F6 C4 C3 F4 50.1(3) . . . . ?
F6 C4 C3 F3 -68.2(3) . . . . ?
C5 C4 C3 C2 50.2(3) . . . . ?
C5 C4 C3 F4 -70.9(3) . . . . ?
C5 C4 C3 F3 170.8(2) . . . . ?
F5 C4 C3 C2 -70.7(3) . . . . ?
F5 C4 C3 F4 168.2(2) . . . . ?
F5 C4 C3 F3 49.8(3) . . . . ?
O4 C7 C12 F20 69.3(3) . . . . ?
O4 C7 C12 F19 -47.8(3) . . . . ?
O4 C7 C12 C11 -168.9(2) . . . . ?
O3 C7 C12 F20 -53.2(2) . . . . ?
O3 C7 C12 F19 -170.25(18) . . . . ?
O3 C7 C12 C11 68.7(2) . . . . ?
F9 C6 C5 C4 -71.0(3) . . . . ?
F9 C6 C5 F8 168.11(18) . . . . ?
F9 C6 C5 F7 49.7(2) . . . . ?
C9 C8 C7 O4 170.3(2) . . . . ?
C9 C8 C7 O3 -66.3(3) . . . . ?
C9 C8 C7 C12 50.0(3) . . . . ?
C9 C10 C11 F18 71.7(3) . . . . ?
C9 C10 C11 F17 -170.4(2) . . . . ?
C9 C10 C11 C12 -49.2(3) . . . . ?
F8 C5 C4 F6 -50.7(3) . . . . ?
F8 C5 C4 F5 -168.9(2) . . . . ?
F8 C5 C4 C3 70.2(3) . . . . ?
C8 C9 C10 F16 171.1(2) . . . . ?
C8 C9 C10 F15 -70.6(3) . . . . ?
C8 C9 C10 C11 49.5(3) . . . . ?
C8 C7 C12 F20 -172.6(2) . . . . ?
C8 C7 C12 F19 70.3(3) . . . . ?
C8 C7 C12 C11 -50.8(3) . . . . ?
F7 C5 C4 F6 67.8(3) . . . . ?
F7 C5 C4 F5 -50.4(3) . . . . ?
F7 C5 C4 C3 -171.3(2) . . . . ?
C7 C12 C11 C10 50.7(3) . . . . ?
C7 C12 C11 F18 -70.0(3) . . . . ?
C7 C12 C11 F17 171.3(2) . . . . ?
F10 C6 C5 C4 171.9(2) . . . . ?
F10 C6 C5 F8 51.1(3) . . . . ?
F10 C6 C5 F7 -67.3(3) . . . . ?
C10 C9 C8 C7 -50.4(3) . . . . ?
C10 C9 C8 F12 -170.9(2) . . . . ?
C10 C9 C8 F11 71.6(3) . . . . ?
F20 C12 C11 C10 172.3(2) . . . . ?
F20 C12 C11 F18 51.6(3) . . . . ?
F20 C12 C11 F17 -67.1(3) . . . . ?
F19 C12 C11 C10 -70.9(3) . . . . ?
F19 C12 C11 F18 168.4(2) . . . . ?
F19 C12 C11 F17 49.6(3) . . . . ?
F16 C10 C11 F18 -50.0(3) . . . . ?
F16 C10 C11 F17 67.9(3) . . . . ?
F16 C10 C11 C12 -170.9(2) . . . . ?
F15 C10 C11 F18 -168.2(2) . . . . ?
F15 C10 C11 F17 -50.3(3) . . . . ?
F15 C10 C11 C12 70.9(3) . . . . ?
F14 C9 C8 C7 70.6(3) . . . . ?
F14 C9 C8 F12 -50.0(3) . . . . ?
F14 C9 C8 F11 -167.5(2) . . . . ?
F14 C9 C10 F16 50.4(3) . . . . ?
F14 C9 C10 F15 168.69(19) . . . . ?
F14 C9 C10 C11 -71.2(3) . . . . ?
F13 C9 C8 C7 -171.6(2) . . . . ?
F13 C9 C8 F12 67.8(3) . . . . ?
F13 C9 C8 F11 -49.7(3) . . . . ?
F13 C9 C10 F16 -67.6(3) . . . . ?
F13 C9 C10 F15 50.7(3) . . . . ?
F13 C9 C10 C11 170.8(2) . . . . ?
F12 C8 C7 O4 -68.8(3) . . . . ?
F12 C8 C7 O3 54.6(3) . . . . ?
F12 C8 C7 C12 171.0(2) . . . . ?
F11 C8 C7 O4 48.8(3) . . . . ?
F11 C8 C7 O3 172.2(2) . . . . ?
F11 C8 C7 C12 -71.4(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT111_pca21_b             
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit  
RESPONSE: Pbca does not lead to a suitable model.
;
_vrf_PLAT112_pca21_b             
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem         b        100 %Fit  
RESPONSE: Pbca does not lead to a suitable model.
;
_vrf_PLAT113_pca21_b             
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group       Pbca Check 
RESPONSE: Pbca does not lead to a suitable model.
;
####################################################################### 
# 
# 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_p21c
_database_code_depnum_ccdc_archive 'CCDC 1839048'
_audit_update_record             
;
2018-04-23 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 F11 O, C4 H12 N'
_chemical_formula_sum            'C10 H12 F11 N O'
_chemical_formula_weight         371.21
_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'
N N 0.0061 0.0033 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.4929(2)
_cell_length_b                   10.3291(2)
_cell_length_c                   18.0550(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.4750(10)
_cell_angle_gamma                90
_cell_volume                     1393.11(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8771
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.913
_cell_measurement_theta_min      3.37
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.7080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0781 before and 0.0412 after correction. The Ratio of minimum to maximum transmission is 0.9491. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29035
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.022
_diffrn_reflns_theta_min         2.273
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'fixed-chi two circle goniometer'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec Mo I\ms'
_diffrn_source_voltage           0.6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3426
_reflns_number_total             4062
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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, 2015)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4062
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.073
_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)+(0.0381P)²+0.5962P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, All F(H,H,H) groups
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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
F2 F 0.95498(10) 0.95954(7) 0.34337(4) 0.02488(17) Uani 1 1 d . . . . .
F1 F 1.05144(10) 0.85552(8) 0.44320(4) 0.02702(17) Uani 1 1 d . . . . .
F11 F 0.69207(9) 0.78842(7) 0.30822(4) 0.02173(15) Uani 1 1 d . . . . .
F6 F 1.16776(10) 0.60202(8) 0.42220(4) 0.02756(17) Uani 1 1 d . . . . .
F5 F 1.16012(10) 0.53791(7) 0.30725(4) 0.02636(17) Uani 1 1 d . . . . .
F4 F 1.01780(10) 0.75783(8) 0.25741(4) 0.02530(17) Uani 1 1 d . . . . .
F7 F 0.90064(12) 0.43943(7) 0.39410(5) 0.03253(19) Uani 1 1 d . . . . .
F3 F 1.24837(10) 0.79447(8) 0.33507(5) 0.03095(19) Uani 1 1 d . . . . .
F9 F 0.83540(13) 0.63499(8) 0.47918(4) 0.0345(2) Uani 1 1 d . . . . .
O1 O 0.68034(12) 0.86426(9) 0.42787(5) 0.02183(18) Uani 1 1 d . . . . .
F10 F 0.60212(11) 0.60026(8) 0.40204(6) 0.0379(2) Uani 1 1 d . . . . .
C2 C 0.96176(14) 0.84141(11) 0.37572(6) 0.0164(2) Uani 1 1 d . . . . .
C1 C 0.76769(14) 0.79383(11) 0.38688(6) 0.0157(2) Uani 1 1 d . . . . .
N N 0.49486(12) 0.17862(9) 0.38330(5) 0.01472(18) Uani 1 1 d . . . . .
C3 C 1.07680(15) 0.75316(11) 0.32982(7) 0.0185(2) Uani 1 1 d . . . . .
C5 C 0.88581(16) 0.55756(11) 0.36184(7) 0.0200(2) Uani 1 1 d . . . . .
C6 C 0.77063(16) 0.64696(12) 0.40721(7) 0.0210(2) Uani 1 1 d . . . . .
C4 C 1.07582(15) 0.61110(11) 0.35549(6) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.62508(16) 0.17832(13) 0.45072(7) 0.0203(2) Uani 1 1 d . . . . .
H9A H 0.681(2) 0.0930(17) 0.4542(9) 0.030 Uiso 1 1 d R . . . .
H9B H 0.712(2) 0.2445(17) 0.4449(9) 0.030 Uiso 1 1 d R . . . .
H9C H 0.563(2) 0.1979(17) 0.4937(10) 0.030 Uiso 1 1 d R . . . .
C11 C 0.35158(16) 0.08089(13) 0.39377(7) 0.0219(2) Uani 1 1 d . . . . .
H11A H 0.410(2) -0.0014(18) 0.3992(10) 0.033 Uiso 1 1 d R . . . .
H11B H 0.296(2) 0.1020(17) 0.4379(10) 0.033 Uiso 1 1 d R . . . .
H11C H 0.269(2) 0.0837(18) 0.3500(10) 0.033 Uiso 1 1 d R . . . .
C12 C 0.41226(19) 0.30925(12) 0.37261(7) 0.0243(2) Uani 1 1 d . . . . .
H12A H 0.355(2) 0.3311(18) 0.4166(10) 0.036 Uiso 1 1 d R . . . .
H12B H 0.509(2) 0.3714(18) 0.3663(10) 0.036 Uiso 1 1 d R . . . .
H12C H 0.331(2) 0.3060(18) 0.3289(10) 0.036 Uiso 1 1 d R . . . .
C10 C 0.59036(17) 0.14330(13) 0.31651(7) 0.0219(2) Uani 1 1 d . . . . .
F8 F 0.80666(10) 0.54011(8) 0.29320(4) 0.02782(17) Uani 1 1 d . . . . .
H10A H 0.684(3) 0.2054(19) 0.3135(10) 0.042 Uiso 1 1 d R . . . .
H10B H 0.642(3) 0.058(2) 0.3243(10) 0.042 Uiso 1 1 d R . . . .
H10C H 0.508(3) 0.1500(19) 0.2725(10) 0.042 Uiso 1 1 d 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
F2 C2 1.3521(13) . ?
F1 C2 1.3525(13) . ?
F11 C1 1.4886(12) . ?
F6 C4 1.3432(13) . ?
F5 C4 1.3473(13) . ?
F4 C3 1.3479(14) . ?
F7 C5 1.3528(14) . ?
F3 C3 1.3508(13) . ?
F9 C6 1.3568(14) . ?
O1 C1 1.2573(13) . ?
F10 C6 1.3481(14) . ?
C2 C1 1.5628(15) . ?
C2 C3 1.5402(16) . ?
C1 C6 1.5607(16) . ?
N C9 1.4994(14) . ?
N C11 1.4963(15) . ?
N C12 1.4907(15) . ?
N C10 1.4947(14) . ?
C3 C4 1.5390(16) . ?
C5 C6 1.5423(16) . ?
C5 C4 1.5400(16) . ?
C5 F8 1.3437(14) . ?

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
F2 C2 F1 106.93(9) . . ?
F2 C2 C1 109.60(9) . . ?
F2 C2 C3 107.78(9) . . ?
F1 C2 C1 108.64(9) . . ?
F1 C2 C3 106.79(9) . . ?
C3 C2 C1 116.66(9) . . ?
F11 C1 C2 100.23(8) . . ?
F11 C1 C6 100.68(8) . . ?
O1 C1 F11 113.98(9) . . ?
O1 C1 C2 115.23(10) . . ?
O1 C1 C6 114.99(9) . . ?
C6 C1 C2 109.86(9) . . ?
C11 N C9 108.90(9) . . ?
C12 N C9 110.14(9) . . ?
C12 N C11 109.41(10) . . ?
C12 N C10 109.66(9) . . ?
C10 N C9 109.41(9) . . ?
C10 N C11 109.30(9) . . ?
F4 C3 F3 107.16(9) . . ?
F4 C3 C2 110.23(9) . . ?
F4 C3 C4 108.50(9) . . ?
F3 C3 C2 110.17(9) . . ?
F3 C3 C4 107.87(9) . . ?
C4 C3 C2 112.72(9) . . ?
F7 C5 C6 109.99(10) . . ?
F7 C5 C4 108.09(10) . . ?
C4 C5 C6 112.54(9) . . ?
F8 C5 F7 106.95(9) . . ?
F8 C5 C6 110.20(10) . . ?
F8 C5 C4 108.88(9) . . ?
F9 C6 C1 108.14(10) . . ?
F9 C6 C5 106.32(10) . . ?
F10 C6 F9 107.27(10) . . ?
F10 C6 C1 109.60(10) . . ?
F10 C6 C5 107.99(10) . . ?
C5 C6 C1 117.08(9) . . ?
F6 C4 F5 107.87(9) . . ?
F6 C4 C3 108.81(9) . . ?
F6 C4 C5 108.70(9) . . ?
F5 C4 C3 109.08(9) . . ?
F5 C4 C5 109.23(9) . . ?
C3 C4 C5 113.02(9) . . ?

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
F2 C2 C1 F11 61.90(10) . . . . ?
F2 C2 C1 O1 -60.89(12) . . . . ?
F2 C2 C1 C6 167.29(9) . . . . ?
F2 C2 C3 F4 -51.57(12) . . . . ?
F2 C2 C3 F3 66.49(12) . . . . ?
F2 C2 C3 C4 -172.96(9) . . . . ?
F1 C2 C1 F11 178.42(8) . . . . ?
F1 C2 C1 O1 55.63(12) . . . . ?
F1 C2 C1 C6 -76.19(11) . . . . ?
F1 C2 C3 F4 -166.16(9) . . . . ?
F1 C2 C3 F3 -48.10(12) . . . . ?
F1 C2 C3 C4 72.45(12) . . . . ?
F11 C1 C6 F9 -179.20(8) . . . . ?
F11 C1 C6 F10 -62.57(11) . . . . ?
F11 C1 C6 C5 60.82(12) . . . . ?
F4 C3 C4 F6 167.46(8) . . . . ?
F4 C3 C4 F5 50.02(12) . . . . ?
F4 C3 C4 C5 -71.69(11) . . . . ?
F7 C5 C6 F9 48.15(13) . . . . ?
F7 C5 C6 F10 -66.71(13) . . . . ?
F7 C5 C6 C1 169.08(10) . . . . ?
F7 C5 C4 F6 -50.91(12) . . . . ?
F7 C5 C4 F5 66.56(12) . . . . ?
F7 C5 C4 C3 -171.82(9) . . . . ?
F3 C3 C4 F6 51.69(12) . . . . ?
F3 C3 C4 F5 -65.76(12) . . . . ?
F3 C3 C4 C5 172.53(9) . . . . ?
O1 C1 C6 F9 -56.23(13) . . . . ?
O1 C1 C6 F10 60.41(13) . . . . ?
O1 C1 C6 C5 -176.20(10) . . . . ?
C2 C1 C6 F9 75.72(11) . . . . ?
C2 C1 C6 F10 -167.65(9) . . . . ?
C2 C1 C6 C5 -44.26(13) . . . . ?
C2 C3 C4 F6 -70.17(12) . . . . ?
C2 C3 C4 F5 172.39(9) . . . . ?
C2 C3 C4 C5 50.67(13) . . . . ?
C1 C2 C3 F4 72.16(12) . . . . ?
C1 C2 C3 F3 -169.78(9) . . . . ?
C1 C2 C3 C4 -49.23(13) . . . . ?
C3 C2 C1 F11 -60.88(11) . . . . ?
C3 C2 C1 O1 176.33(10) . . . . ?
C3 C2 C1 C6 44.50(13) . . . . ?
C6 C5 C4 F6 70.76(12) . . . . ?
C6 C5 C4 F5 -171.77(9) . . . . ?
C6 C5 C4 C3 -50.14(13) . . . . ?
C4 C5 C6 F9 -72.44(12) . . . . ?
C4 C5 C6 F10 172.70(10) . . . . ?
C4 C5 C6 C1 48.49(14) . . . . ?
F8 C5 C6 F9 165.82(9) . . . . ?
F8 C5 C6 F10 50.96(13) . . . . ?
F8 C5 C6 C1 -73.25(13) . . . . ?
F8 C5 C4 F6 -166.75(9) . . . . ?
F8 C5 C4 F5 -49.29(12) . . . . ?
F8 C5 C4 C3 72.34(12) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems 700'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_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_jasc31_3_100_00
_database_code_depnum_ccdc_archive 'CCDC 1848204'
_audit_update_record             
;
2018-06-08 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             2017-04-06
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '3(C7 H F13 O), 2(H2 O)'
_chemical_formula_sum            'C21 H7 F39 O5'
_chemical_formula_weight         1080.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H4F42O2
_chemical_oxdiff_usercomment     
'in-situ grown at 235.6 K from a mixture with hexane by manually generating a crystal seed and chilling to 200 K with 20 K/h and to 100 K with 50 K/h'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0390(4)
_cell_length_b                   22.2491(13)
_cell_length_c                   21.3552(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.561(5)
_cell_angle_gamma                90
_cell_volume                     3338.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14364
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      25.9910
_cell_measurement_theta_min      1.8110
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cylindrically
_exptl_crystal_F_000             2096
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 8 5 0.1606
10 -8 -5 0.1606
1 0 30 0.1213
-1 0 -30 0.1213
-2 -30 1 0.1147
2 30 -1 0.1147
-2 -23 -19 0.1246
2 23 19 0.1246
1 20 -23 0.1213
-1 -20 23 0.1213

_exptl_crystal_recrystallization_method 
"'in-situ grown at 235.6 K from a mixture with hexane by manually generating a crystal seed and chilling to 200 K with 20 K/h and to 100 K with 50 K/h'"
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.243
_exptl_crystal_size_min          0.229
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-10.0002 8.0107 4.9900 0.0141 -0.0072 1.0444
10.0002 -8.0107 -4.9900 -0.0141 0.0072 -1.0444
1.0025 0.0284 29.9924 0.8583 -0.5307 -0.0130
-1.0025 -0.0284 -29.9924 -0.8583 0.5307 0.0130
-1.9918 -30.0141 1.0272 -0.5141 -0.8315 -0.0358
1.9918 30.0141 -1.0272 0.5141 0.8315 0.0358
-1.9954 -23.0296 -18.9741 -0.9548 -0.2854 -0.0375
1.9954 23.0296 18.9741 0.9548 0.2854 0.0375
0.9926 19.9882 -23.0124 -0.2857 0.9546 -0.0062
-0.9926 -19.9882 23.0124 0.2857 -0.9546 0.0062

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            75798
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.831
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0951
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  45.00   1.00   16.00    --  -23.50  57.00-120.00   87
  2  ω     -4.00  94.00   1.00   16.00    --   25.11  77.00   0.00   98
  3  ω     -4.00  94.00   1.00   16.00    --   25.11  77.00  90.00   98
  4  ω    -20.00  66.00   1.00   16.00    --   25.11 -99.00-120.00   86
  5  ω    -44.00  54.00   1.00   16.00    --   25.11 -77.00 -30.00   98
  6  ω      7.00  94.00   1.00   16.00    --   25.11  57.00 -60.00   87
  7  ω    -45.00  47.00   1.00   16.00    --   25.11 -38.00  30.00   92
  8  ω     -4.00  94.00   1.00   16.00    --   25.11  77.00-180.00   98
  9  ω    -45.00  47.00   1.00   16.00    --   25.11 -38.00 120.00   92
 10  ω      8.00  86.00   1.00   16.00    --   25.11-134.00 135.36   78
 11  ω    -97.00 -35.00   1.00   16.00    --  -23.50-178.00  90.00   62
 12  ω    -95.00  48.00   1.00   16.00    --  -23.50   0.00-180.00  143
 13  ω    -95.00  42.00   1.00   16.00    --  -23.50   0.00-150.00  137
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0255606000
_diffrn_orient_matrix_UB_12      0.0163817000
_diffrn_orient_matrix_UB_13      0.0277477000
_diffrn_orient_matrix_UB_21      0.0126914000
_diffrn_orient_matrix_UB_22      0.0262404000
_diffrn_orient_matrix_UB_23      -0.0181430000
_diffrn_orient_matrix_UB_31      -0.0968616000
_diffrn_orient_matrix_UB_32      0.0077179000
_diffrn_orient_matrix_UB_33      0.0027957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5005
_reflns_number_total             6588
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         6588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.052
_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)+(0.0266P)²+3.6787P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0825
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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 1.16262(19) 0.39663(7) 0.35584(7) 0.0294(4) Uani 1 1 d . . . . .
F2 F 1.0657(2) 0.47397(7) 0.29957(7) 0.0299(4) Uani 1 1 d . . . . .
F3 F 1.1066(2) 0.50344(7) 0.41793(8) 0.0360(4) Uani 1 1 d . . . . .
F4 F 0.9502(2) 0.42520(7) 0.44771(7) 0.0288(3) Uani 1 1 d . . . . .
F5 F 0.8038(2) 0.54818(7) 0.35567(8) 0.0360(4) Uani 1 1 d . . . . .
F6 F 0.7322(2) 0.52207(7) 0.44981(8) 0.0394(4) Uani 1 1 d . . . . .
F7 F 0.4626(2) 0.50009(7) 0.35090(8) 0.0352(4) Uani 1 1 d . . . . .
F8 F 0.5591(2) 0.42331(7) 0.40724(7) 0.0278(3) Uani 1 1 d . . . . .
F9 F 0.5135(2) 0.39403(7) 0.28812(7) 0.0320(4) Uani 1 1 d . . . . .
F10 F 0.6734(2) 0.47202(7) 0.25886(7) 0.0322(4) Uani 1 1 d . . . . .
F11 F 0.9360(3) 0.40819(8) 0.20466(7) 0.0460(5) Uani 1 1 d . . . . .
F12 F 1.0514(2) 0.33200(8) 0.25570(8) 0.0412(4) Uani 1 1 d . . . . .
F13 F 0.7577(3) 0.33279(8) 0.22332(8) 0.0439(4) Uani 1 1 d . . . . .
O1 O 0.8078(3) 0.34579(8) 0.35095(8) 0.0206(4) Uani 1 1 d . . . . .
H1 H 0.900(4) 0.3289(13) 0.3582(13) 0.028(9) Uiso 1 1 d . . . . .
C1 C 0.8471(3) 0.39328(11) 0.31118(11) 0.0189(5) Uani 1 1 d . . . . .
C2 C 1.0126(3) 0.43254(11) 0.34087(12) 0.0218(5) Uani 1 1 d . . . . .
C3 C 0.9632(4) 0.46554(11) 0.40126(12) 0.0238(6) Uani 1 1 d . . . . .
C4 C 0.7772(4) 0.50114(12) 0.39376(12) 0.0268(6) Uani 1 1 d . . . . .
C5 C 0.6113(3) 0.46358(11) 0.36498(12) 0.0236(6) Uani 1 1 d . . . . .
C6 C 0.6611(3) 0.43057(11) 0.30450(12) 0.0223(5) Uani 1 1 d . . . . .
C7 C 0.8977(4) 0.36723(13) 0.24670(13) 0.0311(6) Uani 1 1 d . . . . .
F27 F 1.15857(19) 0.12936(7) 0.36805(7) 0.0279(3) Uani 1 1 d . . . . .
F28 F 1.0631(2) 0.05427(7) 0.30839(7) 0.0292(4) Uani 1 1 d . . . . .
F29 F 1.0903(2) 0.02144(8) 0.42593(8) 0.0420(4) Uani 1 1 d . . . . .
F30 F 0.9333(2) 0.09928(7) 0.45629(7) 0.0326(4) Uani 1 1 d . . . . .
F31 F 0.7917(2) -0.02050(7) 0.35863(8) 0.0379(4) Uani 1 1 d . . . . .
F32 F 0.7104(3) 0.00287(8) 0.45232(8) 0.0451(5) Uani 1 1 d . . . . .
F33 F 0.4529(2) 0.02960(7) 0.35223(8) 0.0342(4) Uani 1 1 d . . . . .
F34 F 0.5495(2) 0.10432(7) 0.41169(7) 0.0302(4) Uani 1 1 d . . . . .
F35 F 0.5149(2) 0.13692(7) 0.29315(7) 0.0328(4) Uani 1 1 d . . . . .
F36 F 0.6758(2) 0.05933(7) 0.26333(7) 0.0316(4) Uani 1 1 d . . . . .
F37 F 0.7726(2) 0.19946(8) 0.23350(7) 0.0408(4) Uani 1 1 d . . . . .
F38 F 0.9465(2) 0.12337(8) 0.21426(7) 0.0394(4) Uani 1 1 d . . . . .
F39 F 1.0642(2) 0.19712(8) 0.26924(7) 0.0377(4) Uani 1 1 d . . . . .
O3 O 0.8073(3) 0.18220(8) 0.36076(8) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.891(5) 0.2011(16) 0.3677(16) 0.048(11) Uiso 1 1 d . . . . .
C15 C 0.8471(3) 0.13575(11) 0.32013(11) 0.0196(5) Uani 1 1 d . . . . .
C16 C 1.0072(3) 0.09474(11) 0.35015(12) 0.0219(5) Uani 1 1 d . . . . .
C17 C 0.9511(4) 0.06050(12) 0.40897(12) 0.0269(6) Uani 1 1 d . . . . .
C18 C 0.7633(4) 0.02547(12) 0.39788(13) 0.0285(6) Uani 1 1 d . . . . .
C19 C 0.6028(3) 0.06469(12) 0.36847(12) 0.0246(6) Uani 1 1 d . . . . .
C20 C 0.6595(4) 0.09941(12) 0.30983(12) 0.0241(6) Uani 1 1 d . . . . .
C21 C 0.9080(4) 0.16348(13) 0.25740(12) 0.0283(6) Uani 1 1 d . . . . .
F14 F 0.4287(2) 0.29586(8) 0.64844(7) 0.0335(4) Uani 1 1 d . . . . .
F15 F 0.2402(2) 0.34344(7) 0.58056(8) 0.0327(4) Uani 1 1 d . . . . .
F16 F 0.06717(19) 0.24439(7) 0.54274(6) 0.0255(3) Uani 1 1 d . . . . .
F17 F 0.0842(2) 0.25095(7) 0.64438(7) 0.0315(4) Uani 1 1 d . . . . .
F18 F 0.1313(2) 0.13775(7) 0.59106(8) 0.0381(4) Uani 1 1 d . . . . .
F19 F 0.3603(2) 0.17079(8) 0.65563(7) 0.0365(4) Uani 1 1 d . . . . .
F20 F 0.3212(2) 0.16374(7) 0.49219(7) 0.0309(4) Uani 1 1 d . . . . .
F21 F 0.5068(2) 0.11516(7) 0.56013(8) 0.0385(4) Uani 1 1 d . . . . .
F22 F 0.67070(19) 0.20704(7) 0.49669(7) 0.0256(3) Uani 1 1 d . . . . .
F23 F 0.6844(2) 0.21294(7) 0.59878(7) 0.0275(3) Uani 1 1 d . . . . .
F24 F 0.7550(2) 0.32810(7) 0.59597(7) 0.0343(4) Uani 1 1 d . . . . .
F25 F 0.7476(2) 0.32491(7) 0.49526(7) 0.0304(4) Uani 1 1 d . . . . .
F26 F 0.5646(2) 0.38572(7) 0.54118(8) 0.0363(4) Uani 1 1 d . . . . .
O2 O 0.3777(2) 0.28844(8) 0.48346(8) 0.0219(4) Uani 1 1 d . . . . .
H2 H 0.443(5) 0.2834(15) 0.4552(15) 0.040(10) Uiso 1 1 d . . . . .
C8 C 0.4815(3) 0.28244(11) 0.54068(11) 0.0181(5) Uani 1 1 d . . . . .
C9 C 0.3360(3) 0.29213(12) 0.59133(11) 0.0224(5) Uani 1 1 d . . . . .
C10 C 0.1867(3) 0.24147(12) 0.59435(11) 0.0226(5) Uani 1 1 d . . . . .
C11 C 0.2724(4) 0.17833(12) 0.59841(12) 0.0263(6) Uani 1 1 d . . . . .
C12 C 0.4169(4) 0.16753(11) 0.54860(12) 0.0248(6) Uani 1 1 d . . . . .
C13 C 0.5677(3) 0.21782(11) 0.54671(11) 0.0200(5) Uani 1 1 d . . . . .
C14 C 0.6406(4) 0.33109(12) 0.54449(12) 0.0242(6) Uani 1 1 d . . . . .
O4 O 1.0779(3) 0.26574(9) 0.39109(10) 0.0228(4) Uani 1 1 d . . . . .
H4A H 1.161(5) 0.2648(14) 0.3733(15) 0.033(10) Uiso 1 1 d . . . . .
H4B H 1.114(5) 0.2680(17) 0.428(2) 0.064(13) Uiso 1 1 d . . . . .
O5 O 0.4832(3) 0.26603(10) 0.36914(9) 0.0240(4) Uani 1 1 d . . . . .
H5A H 0.539(4) 0.2348(15) 0.3612(14) 0.034(9) Uiso 1 1 d . . . . .
H5B H 0.536(5) 0.2904(17) 0.3529(17) 0.048(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 C2 1.347(3) . ?
F2 C2 1.345(3) . ?
F3 C3 1.346(3) . ?
F4 C3 1.345(3) . ?
F5 C4 1.346(3) . ?
F6 C4 1.340(3) . ?
F7 C5 1.344(3) . ?
F8 C5 1.339(3) . ?
F9 C6 1.348(3) . ?
F10 C6 1.348(3) . ?
F11 C7 1.319(3) . ?
F12 C7 1.340(3) . ?
F13 C7 1.321(3) . ?
O1 H1 0.76(3) . ?
O1 C1 1.394(3) . ?
C1 C2 1.559(3) . ?
C1 C6 1.549(3) . ?
C1 C7 1.556(3) . ?
C2 C3 1.542(4) . ?
C3 C4 1.530(4) . ?
C4 C5 1.533(4) . ?
C5 C6 1.545(4) . ?
F27 C16 1.351(3) . ?
F28 C16 1.343(3) . ?
F29 C17 1.342(3) . ?
F30 C17 1.341(3) . ?
F31 C18 1.345(3) . ?
F32 C18 1.340(3) . ?
F33 C19 1.341(3) . ?
F34 C19 1.347(3) . ?
F35 C20 1.347(3) . ?
F36 C20 1.345(3) . ?
F37 C21 1.323(3) . ?
F38 C21 1.323(3) . ?
F39 C21 1.341(3) . ?
O3 H3 0.73(3) . ?
O3 C15 1.389(3) . ?
C15 C16 1.557(3) . ?
C15 C20 1.552(3) . ?
C15 C21 1.559(4) . ?
C16 C17 1.541(4) . ?
C17 C18 1.540(4) . ?
C18 C19 1.531(4) . ?
C19 C20 1.545(4) . ?
F14 C9 1.350(3) . ?
F15 C9 1.338(3) . ?
F16 C10 1.346(3) . ?
F17 C10 1.343(3) . ?
F18 C11 1.344(3) . ?
F19 C11 1.346(3) . ?
F20 C12 1.346(3) . ?
F21 C12 1.341(3) . ?
F22 C13 1.349(3) . ?
F23 C13 1.345(3) . ?
F24 C14 1.324(3) . ?
F25 C14 1.338(3) . ?
F26 C14 1.328(3) . ?
O2 H2 0.79(3) . ?
O2 C8 1.390(3) . ?
C8 C9 1.550(3) . ?
C8 C13 1.563(3) . ?
C8 C14 1.556(3) . ?
C9 C10 1.545(4) . ?
C10 C11 1.529(4) . ?
C11 C12 1.536(4) . ?
C12 C13 1.544(3) . ?
O4 H4A 0.72(3) . ?
O4 H4B 0.82(4) . ?
O5 H5A 0.82(3) . ?
O5 H5B 0.75(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
C1 O1 H1 107(2) . . ?
O1 C1 C2 110.38(19) . . ?
O1 C1 C6 105.29(19) . . ?
O1 C1 C7 108.8(2) . . ?
C6 C1 C2 110.1(2) . . ?
C6 C1 C7 110.9(2) . . ?
C7 C1 C2 111.2(2) . . ?
F1 C2 C1 108.6(2) . . ?
F1 C2 C3 107.3(2) . . ?
F2 C2 F1 108.45(19) . . ?
F2 C2 C1 110.4(2) . . ?
F2 C2 C3 108.0(2) . . ?
C3 C2 C1 113.90(19) . . ?
F3 C3 C2 108.4(2) . . ?
F3 C3 C4 109.0(2) . . ?
F4 C3 F3 107.9(2) . . ?
F4 C3 C2 109.1(2) . . ?
F4 C3 C4 109.0(2) . . ?
C4 C3 C2 113.3(2) . . ?
F5 C4 C3 108.4(2) . . ?
F5 C4 C5 108.2(2) . . ?
F6 C4 F5 108.6(2) . . ?
F6 C4 C3 109.5(2) . . ?
F6 C4 C5 109.3(2) . . ?
C3 C4 C5 112.7(2) . . ?
F7 C5 C4 108.9(2) . . ?
F7 C5 C6 108.3(2) . . ?
F8 C5 F7 108.21(19) . . ?
F8 C5 C4 109.2(2) . . ?
F8 C5 C6 109.4(2) . . ?
C4 C5 C6 112.8(2) . . ?
F9 C6 F10 107.95(19) . . ?
F9 C6 C1 109.5(2) . . ?
F9 C6 C5 107.0(2) . . ?
F10 C6 C1 109.92(19) . . ?
F10 C6 C5 107.9(2) . . ?
C5 C6 C1 114.31(19) . . ?
F11 C7 F12 107.7(2) . . ?
F11 C7 F13 108.8(2) . . ?
F11 C7 C1 114.4(2) . . ?
F12 C7 C1 108.6(2) . . ?
F13 C7 F12 106.9(2) . . ?
F13 C7 C1 110.1(2) . . ?
C15 O3 H3 111(3) . . ?
O3 C15 C16 110.35(19) . . ?
O3 C15 C20 105.87(19) . . ?
O3 C15 C21 108.6(2) . . ?
C16 C15 C21 110.8(2) . . ?
C20 C15 C16 109.9(2) . . ?
C20 C15 C21 111.2(2) . . ?
F27 C16 C15 108.7(2) . . ?
F27 C16 C17 106.8(2) . . ?
F28 C16 F27 108.16(19) . . ?
F28 C16 C15 110.72(19) . . ?
F28 C16 C17 108.1(2) . . ?
C17 C16 C15 114.2(2) . . ?
F29 C17 C16 108.7(2) . . ?
F29 C17 C18 108.6(2) . . ?
F30 C17 F29 108.3(2) . . ?
F30 C17 C16 109.7(2) . . ?
F30 C17 C18 108.8(2) . . ?
C18 C17 C16 112.7(2) . . ?
F31 C18 C17 108.7(2) . . ?
F31 C18 C19 108.2(2) . . ?
F32 C18 F31 108.4(2) . . ?
F32 C18 C17 109.8(2) . . ?
F32 C18 C19 109.4(2) . . ?
C19 C18 C17 112.3(2) . . ?
F33 C19 F34 108.07(19) . . ?
F33 C19 C18 108.9(2) . . ?
F33 C19 C20 108.7(2) . . ?
F34 C19 C18 108.8(2) . . ?
F34 C19 C20 109.0(2) . . ?
C18 C19 C20 113.4(2) . . ?
F35 C20 C15 109.7(2) . . ?
F35 C20 C19 107.2(2) . . ?
F36 C20 F35 108.25(19) . . ?
F36 C20 C15 109.8(2) . . ?
F36 C20 C19 107.8(2) . . ?
C19 C20 C15 114.0(2) . . ?
F37 C21 F38 108.3(2) . . ?
F37 C21 F39 107.3(2) . . ?
F37 C21 C15 109.9(2) . . ?
F38 C21 F39 107.9(2) . . ?
F38 C21 C15 114.3(2) . . ?
F39 C21 C15 109.0(2) . . ?
C8 O2 H2 111(2) . . ?
O2 C8 C9 105.44(19) . . ?
O2 C8 C13 109.92(19) . . ?
O2 C8 C14 108.43(19) . . ?
C9 C8 C13 109.91(19) . . ?
C9 C8 C14 111.8(2) . . ?
C14 C8 C13 111.16(19) . . ?
F14 C9 C8 109.61(19) . . ?
F14 C9 C10 107.4(2) . . ?
F15 C9 F14 108.2(2) . . ?
F15 C9 C8 110.3(2) . . ?
F15 C9 C10 107.0(2) . . ?
C10 C9 C8 114.1(2) . . ?
F16 C10 C9 108.8(2) . . ?
F16 C10 C11 108.4(2) . . ?
F17 C10 F16 107.73(19) . . ?
F17 C10 C9 108.6(2) . . ?
F17 C10 C11 109.2(2) . . ?
C11 C10 C9 113.9(2) . . ?
F18 C11 F19 108.5(2) . . ?
F18 C11 C10 108.9(2) . . ?
F18 C11 C12 109.3(2) . . ?
F19 C11 C10 108.9(2) . . ?
F19 C11 C12 108.8(2) . . ?
C10 C11 C12 112.4(2) . . ?
F20 C12 C11 108.3(2) . . ?
F20 C12 C13 109.2(2) . . ?
F21 C12 F20 108.3(2) . . ?
F21 C12 C11 109.5(2) . . ?
F21 C12 C13 108.5(2) . . ?
C11 C12 C13 113.0(2) . . ?
F22 C13 C8 108.87(19) . . ?
F22 C13 C12 107.2(2) . . ?
F23 C13 F22 108.03(18) . . ?
F23 C13 C8 110.88(19) . . ?
F23 C13 C12 107.8(2) . . ?
C12 C13 C8 113.88(19) . . ?
F24 C14 F25 107.7(2) . . ?
F24 C14 F26 108.2(2) . . ?
F24 C14 C8 114.0(2) . . ?
F25 C14 C8 109.0(2) . . ?
F26 C14 F25 107.3(2) . . ?
F26 C14 C8 110.4(2) . . ?
H4A O4 H4B 107(4) . . ?
H5A O5 H5B 105(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.76(3) 1.98(3) 2.705(3) 160(3) .
O3 H3 O4 0.73(3) 1.99(4) 2.711(3) 168(4) .
O2 H2 O5 0.79(3) 1.92(3) 2.643(3) 153(3) .
O4 H4A O5 0.72(3) 2.27(3) 2.920(3) 150(3) 1_655
O4 H4B F16 0.82(4) 2.54(4) 3.279(3) 150(3) 1_655
O4 H4B O2 0.82(4) 2.18(4) 2.843(2) 137(3) 1_655
O5 H5A F35 0.82(3) 2.62(3) 3.314(3) 144(3) .
O5 H5A O3 0.82(3) 2.22(3) 2.961(3) 150(3) .
O5 H5B O1 0.75(4) 2.28(4) 2.938(3) 147(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 C2 C3 F3 67.3(2) . . . . ?
F1 C2 C3 F4 -49.9(2) . . . . ?
F1 C2 C3 C4 -171.5(2) . . . . ?
F2 C2 C3 F3 -49.4(3) . . . . ?
F2 C2 C3 F4 -166.65(18) . . . . ?
F2 C2 C3 C4 71.7(3) . . . . ?
F3 C3 C4 F5 51.3(3) . . . . ?
F3 C3 C4 F6 -67.0(3) . . . . ?
F3 C3 C4 C5 171.1(2) . . . . ?
F4 C3 C4 F5 168.89(19) . . . . ?
F4 C3 C4 F6 50.6(3) . . . . ?
F4 C3 C4 C5 -71.4(3) . . . . ?
F5 C4 C5 F7 -50.6(3) . . . . ?
F5 C4 C5 F8 -168.54(19) . . . . ?
F5 C4 C5 C6 69.6(3) . . . . ?
F6 C4 C5 F7 67.5(3) . . . . ?
F6 C4 C5 F8 -50.4(3) . . . . ?
F6 C4 C5 C6 -172.2(2) . . . . ?
F7 C5 C6 F9 -66.5(2) . . . . ?
F7 C5 C6 F10 49.5(3) . . . . ?
F7 C5 C6 C1 172.1(2) . . . . ?
F8 C5 C6 F9 51.2(2) . . . . ?
F8 C5 C6 F10 167.18(18) . . . . ?
F8 C5 C6 C1 -70.2(3) . . . . ?
O1 C1 C2 F1 53.9(2) . . . . ?
O1 C1 C2 F2 172.68(19) . . . . ?
O1 C1 C2 C3 -65.7(3) . . . . ?
O1 C1 C6 F9 -51.5(2) . . . . ?
O1 C1 C6 F10 -169.95(19) . . . . ?
O1 C1 C6 C5 68.6(2) . . . . ?
O1 C1 C7 F11 179.4(2) . . . . ?
O1 C1 C7 F12 -60.3(3) . . . . ?
O1 C1 C7 F13 56.4(3) . . . . ?
C1 C2 C3 F3 -172.37(19) . . . . ?
C1 C2 C3 F4 70.4(3) . . . . ?
C1 C2 C3 C4 -51.3(3) . . . . ?
C2 C1 C6 F9 -170.49(19) . . . . ?
C2 C1 C6 F10 71.1(2) . . . . ?
C2 C1 C6 C5 -50.4(3) . . . . ?
C2 C1 C7 F11 -58.8(3) . . . . ?
C2 C1 C7 F12 61.4(3) . . . . ?
C2 C1 C7 F13 178.2(2) . . . . ?
C2 C3 C4 F5 -69.4(3) . . . . ?
C2 C3 C4 F6 172.3(2) . . . . ?
C2 C3 C4 C5 50.3(3) . . . . ?
C3 C4 C5 F7 -170.4(2) . . . . ?
C3 C4 C5 F8 71.7(3) . . . . ?
C3 C4 C5 C6 -50.2(3) . . . . ?
C4 C5 C6 F9 173.0(2) . . . . ?
C4 C5 C6 F10 -71.1(2) . . . . ?
C4 C5 C6 C1 51.5(3) . . . . ?
C6 C1 C2 F1 169.71(19) . . . . ?
C6 C1 C2 F2 -71.5(2) . . . . ?
C6 C1 C2 C3 50.2(3) . . . . ?
C6 C1 C7 F11 64.0(3) . . . . ?
C6 C1 C7 F12 -175.7(2) . . . . ?
C6 C1 C7 F13 -58.9(3) . . . . ?
C7 C1 C2 F1 -67.0(2) . . . . ?
C7 C1 C2 F2 51.8(3) . . . . ?
C7 C1 C2 C3 173.5(2) . . . . ?
C7 C1 C6 F9 66.0(3) . . . . ?
C7 C1 C6 F10 -52.5(3) . . . . ?
C7 C1 C6 C5 -174.0(2) . . . . ?
F27 C16 C17 F29 -67.3(3) . . . . ?
F27 C16 C17 F30 50.9(2) . . . . ?
F27 C16 C17 C18 172.2(2) . . . . ?
F28 C16 C17 F29 48.8(3) . . . . ?
F28 C16 C17 F30 167.04(18) . . . . ?
F28 C16 C17 C18 -71.6(3) . . . . ?
F29 C17 C18 F31 -51.3(3) . . . . ?
F29 C17 C18 F32 67.1(3) . . . . ?
F29 C17 C18 C19 -171.0(2) . . . . ?
F30 C17 C18 F31 -169.0(2) . . . . ?
F30 C17 C18 F32 -50.6(3) . . . . ?
F30 C17 C18 C19 71.3(3) . . . . ?
F31 C18 C19 F33 51.5(3) . . . . ?
F31 C18 C19 F34 169.04(19) . . . . ?
F31 C18 C19 C20 -69.6(3) . . . . ?
F32 C18 C19 F33 -66.4(3) . . . . ?
F32 C18 C19 F34 51.2(3) . . . . ?
F32 C18 C19 C20 172.6(2) . . . . ?
F33 C19 C20 F35 65.7(2) . . . . ?
F33 C19 C20 F36 -50.6(3) . . . . ?
F33 C19 C20 C15 -172.73(19) . . . . ?
F34 C19 C20 F35 -51.8(2) . . . . ?
F34 C19 C20 F36 -168.11(18) . . . . ?
F34 C19 C20 C15 69.7(3) . . . . ?
O3 C15 C16 F27 -53.7(3) . . . . ?
O3 C15 C16 F28 -172.33(19) . . . . ?
O3 C15 C16 C17 65.4(3) . . . . ?
O3 C15 C20 F35 51.3(3) . . . . ?
O3 C15 C20 F36 170.17(19) . . . . ?
O3 C15 C20 C19 -68.8(2) . . . . ?
O3 C15 C21 F37 -56.9(3) . . . . ?
O3 C15 C21 F38 -178.8(2) . . . . ?
O3 C15 C21 F39 60.5(3) . . . . ?
C15 C16 C17 F29 172.5(2) . . . . ?
C15 C16 C17 F30 -69.3(3) . . . . ?
C15 C16 C17 C18 52.1(3) . . . . ?
C16 C15 C20 F35 170.47(19) . . . . ?
C16 C15 C20 F36 -70.7(2) . . . . ?
C16 C15 C20 C19 50.3(3) . . . . ?
C16 C15 C21 F37 -178.3(2) . . . . ?
C16 C15 C21 F38 59.8(3) . . . . ?
C16 C15 C21 F39 -60.9(3) . . . . ?
C16 C17 C18 F31 69.1(3) . . . . ?
C16 C17 C18 F32 -172.5(2) . . . . ?
C16 C17 C18 C19 -50.5(3) . . . . ?
C17 C18 C19 F33 171.5(2) . . . . ?
C17 C18 C19 F34 -71.0(3) . . . . ?
C17 C18 C19 C20 50.4(3) . . . . ?
C18 C19 C20 F35 -173.1(2) . . . . ?
C18 C19 C20 F36 70.6(3) . . . . ?
C18 C19 C20 C15 -51.6(3) . . . . ?
C20 C15 C16 F27 -170.05(19) . . . . ?
C20 C15 C16 F28 71.3(2) . . . . ?
C20 C15 C16 C17 -51.0(3) . . . . ?
C20 C15 C21 F37 59.2(3) . . . . ?
C20 C15 C21 F38 -62.7(3) . . . . ?
C20 C15 C21 F39 176.6(2) . . . . ?
C21 C15 C16 F27 66.7(2) . . . . ?
C21 C15 C16 F28 -52.0(3) . . . . ?
C21 C15 C16 C17 -174.2(2) . . . . ?
C21 C15 C20 F35 -66.5(3) . . . . ?
C21 C15 C20 F36 52.4(3) . . . . ?
C21 C15 C20 C19 173.4(2) . . . . ?
F14 C9 C10 F16 167.91(19) . . . . ?
F14 C9 C10 F17 50.9(3) . . . . ?
F14 C9 C10 C11 -71.1(3) . . . . ?
F15 C9 C10 F16 51.9(2) . . . . ?
F15 C9 C10 F17 -65.2(2) . . . . ?
F15 C9 C10 C11 172.9(2) . . . . ?
F16 C10 C11 F18 -49.3(3) . . . . ?
F16 C10 C11 F19 -167.48(19) . . . . ?
F16 C10 C11 C12 71.9(3) . . . . ?
F17 C10 C11 F18 67.8(3) . . . . ?
F17 C10 C11 F19 -50.4(3) . . . . ?
F17 C10 C11 C12 -171.0(2) . . . . ?
F18 C11 C12 F20 50.1(3) . . . . ?
F18 C11 C12 F21 -67.8(3) . . . . ?
F18 C11 C12 C13 171.1(2) . . . . ?
F19 C11 C12 F20 168.4(2) . . . . ?
F19 C11 C12 F21 50.5(3) . . . . ?
F19 C11 C12 C13 -70.6(3) . . . . ?
F20 C12 C13 F22 -52.2(2) . . . . ?
F20 C12 C13 F23 -168.26(18) . . . . ?
F20 C12 C13 C8 68.3(3) . . . . ?
F21 C12 C13 F22 65.7(2) . . . . ?
F21 C12 C13 F23 -50.4(3) . . . . ?
F21 C12 C13 C8 -173.9(2) . . . . ?
O2 C8 C9 F14 -171.08(19) . . . . ?
O2 C8 C9 F15 -52.0(2) . . . . ?
O2 C8 C9 C10 68.4(2) . . . . ?
O2 C8 C13 F22 55.0(2) . . . . ?
O2 C8 C13 F23 173.72(19) . . . . ?
O2 C8 C13 C12 -64.5(3) . . . . ?
O2 C8 C14 F24 -177.1(2) . . . . ?
O2 C8 C14 F25 -56.6(3) . . . . ?
O2 C8 C14 F26 60.9(3) . . . . ?
C8 C9 C10 F16 -70.4(3) . . . . ?
C8 C9 C10 F17 172.59(19) . . . . ?
C8 C9 C10 C11 50.6(3) . . . . ?
C9 C8 C13 F22 170.63(18) . . . . ?
C9 C8 C13 F23 -70.7(2) . . . . ?
C9 C8 C13 C12 51.1(3) . . . . ?
C9 C8 C14 F24 67.1(3) . . . . ?
C9 C8 C14 F25 -172.45(19) . . . . ?
C9 C8 C14 F26 -54.9(3) . . . . ?
C9 C10 C11 F18 -170.6(2) . . . . ?
C9 C10 C11 F19 71.2(3) . . . . ?
C9 C10 C11 C12 -49.3(3) . . . . ?
C10 C11 C12 F20 -71.0(3) . . . . ?
C10 C11 C12 F21 171.1(2) . . . . ?
C10 C11 C12 C13 50.1(3) . . . . ?
C11 C12 C13 F22 -172.71(19) . . . . ?
C11 C12 C13 F23 71.2(3) . . . . ?
C11 C12 C13 C8 -52.2(3) . . . . ?
C13 C8 C9 F14 70.5(2) . . . . ?
C13 C8 C9 F15 -170.44(19) . . . . ?
C13 C8 C9 C10 -50.0(3) . . . . ?
C13 C8 C14 F24 -56.1(3) . . . . ?
C13 C8 C14 F25 64.3(2) . . . . ?
C13 C8 C14 F26 -178.13(19) . . . . ?
C14 C8 C9 F14 -53.5(3) . . . . ?
C14 C8 C9 F15 65.6(2) . . . . ?
C14 C8 C9 C10 -173.9(2) . . . . ?
C14 C8 C13 F22 -65.0(2) . . . . ?
C14 C8 C13 F23 53.7(3) . . . . ?
C14 C8 C13 C12 175.4(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-05
_olex2_exptl_crystal_mounting_method mounted
_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 1.998
_oxdiff_exptl_absorpt_empirical_full_min 0.605
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-2
