# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1510756'
_audit_update_record             
;
2016-10-19 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;

_audit_creation_date             2016-10-19T13:07:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22 H23 F3 O4'
_chemical_formula_sum            'C22 H23 F3 O4'
_chemical_formula_weight         408.4
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8528(7)
_cell_length_b                   10.3504(8)
_cell_length_c                   14.1556(11)
_cell_angle_alpha                91.588(5)
_cell_angle_beta                 107.369(4)
_cell_angle_gamma                115.303(13)
_cell_volume                     1100.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      29.95
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.1
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.689
_exptl_absorpt_correction_T_max  0.746
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.99

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_number            49415
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.532
_diffrn_reflns_theta_max         30.029
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             6433
_reflns_number_gt                5362
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_reflns_reduction_process 
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V7.68A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement  'SHELXL-2016/5 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   geom
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Structure contains disordered solvent which could not be satisfactorily
 modelled. Likely to be mixture of ethylacetate and hexane. The SQUEEZE 
 procedure (PLATON) was applied to reflection data, but solvent is not 
 included in formula etc, because exact identity was not known.
;

_shelx_SHELXL_version_number     2016/5
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.2780P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6433
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.055

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
F91 F -0.68105(9) -0.26714(7) 0.83273(5) 0.02181(15) Uani 1 1 d . . . . .
F92 F -0.95225(9) -0.37479(7) 0.73018(5) 0.02102(15) Uani 1 1 d . . . . .
F93 F -0.87903(9) -0.44402(7) 0.87193(5) 0.02105(15) Uani 1 1 d . . . . .
O1 O -0.87867(11) -0.22462(10) 1.18174(6) 0.02238(17) Uani 1 1 d . . . . .
O2 O -0.77987(9) -0.18043(8) 0.97740(5) 0.01377(14) Uani 1 1 d . . . . .
O3 O -0.85442(10) -0.10504(8) 0.82319(5) 0.01382(14) Uani 1 1 d . . . . .
O11 O -0.59596(10) -0.18827(9) 1.24658(6) 0.02006(17) Uani 1 1 d . . . . .
C1 C -0.72430(14) -0.15878(12) 1.18943(7) 0.01549(19) Uani 1 1 d . . . . .
C2 C -0.65176(14) -0.03225(12) 1.13756(8) 0.0171(2) Uani 1 1 d . . . . .
H2A H -0.535231 -0.018151 1.13506 0.021 Uiso 1 1 calc R U . . .
H2B H -0.633293 0.057447 1.176458 0.021 Uiso 1 1 calc R U . . .
C3 C -0.77904(13) -0.05915(11) 1.03156(7) 0.01441(19) Uani 1 1 d . . . . .
H3 H -0.900963 -0.087793 1.033675 0.017 Uiso 1 1 calc R U . . .
C4 C -0.72720(14) 0.06954(11) 0.97745(8) 0.01545(19) Uani 1 1 d . . . . .
H4A H -0.603356 0.103464 0.979201 0.019 Uiso 1 1 calc R U . . .
H4B H -0.734262 0.150665 1.011377 0.019 Uiso 1 1 calc R U . . .
C5 C -0.85391(13) 0.02257(11) 0.86855(8) 0.01386(18) Uani 1 1 d . . . . .
H5 H -0.976663 -0.00267 0.867841 0.017 Uiso 1 1 calc R U . . .
C6 C -0.80361(14) 0.13602(11) 0.80300(8) 0.01568(19) Uani 1 1 d . . . . .
H6A H -0.683465 0.159114 0.802033 0.019 Uiso 1 1 calc R U . . .
H6B H -0.798627 0.226082 0.832729 0.019 Uiso 1 1 calc R U . . .
C7 C -0.93557(15) 0.08550(12) 0.69456(8) 0.0179(2) Uani 1 1 d . . . . .
H7A H -0.939103 -0.003686 0.664474 0.021 Uiso 1 1 calc R U . . .
H7B H -1.056048 0.060891 0.695604 0.021 Uiso 1 1 calc R U . . .
C8 C -0.89587(13) -0.22031(11) 0.87678(7) 0.01286(18) Uani 1 1 d . . . . .
C9 C -0.85102(13) -0.32761(11) 0.82762(8) 0.01538(19) Uani 1 1 d . . . . .
C11 C -0.65615(16) -0.30963(13) 1.29786(10) 0.0248(2) Uani 1 1 d . . . . .
H11A H -0.71228 -0.289721 1.34268 0.037 Uiso 1 1 calc R U . . .
H11B H -0.554278 -0.323414 1.337444 0.037 Uiso 1 1 calc R U . . .
H11C H -0.742624 -0.397869 1.24815 0.037 Uiso 1 1 calc R U . . .
C111 C -0.88711(14) 0.19945(11) 0.62957(8) 0.01586(19) Uani 1 1 d . . . . .
C112 C -0.81855(16) 0.18406(13) 0.55562(8) 0.0213(2) Uani 1 1 d . . . . .
H112 H -0.804476 0.099468 0.544874 0.026 Uiso 1 1 calc R U . . .
C113 C -0.77035(17) 0.29044(15) 0.49723(9) 0.0250(2) Uani 1 1 d . . . . .
H113 H -0.722094 0.278705 0.447909 0.03 Uiso 1 1 calc R U . . .
C114 C -0.79261(16) 0.41363(13) 0.51090(9) 0.0238(2) Uani 1 1 d . . . . .
H114 H -0.760769 0.485957 0.470714 0.029 Uiso 1 1 calc R U . . .
C115 C -0.86204(16) 0.43033(12) 0.58404(8) 0.0210(2) Uani 1 1 d . . . . .
H115 H -0.878026 0.514223 0.593645 0.025 Uiso 1 1 calc R U . . .
C116 C -0.90795(14) 0.32473(12) 0.64295(8) 0.0174(2) Uani 1 1 d . . . . .
H116 H -0.954155 0.337621 0.693048 0.021 Uiso 1 1 calc R U . . .
C211 C -1.09221(13) -0.29634(11) 0.86751(8) 0.01363(18) Uani 1 1 d . . . . .
C212 C -1.14380(14) -0.38063(12) 0.93795(8) 0.01655(19) Uani 1 1 d . . . . .
H212 H -1.056499 -0.385113 0.994435 0.02 Uiso 1 1 calc R U . . .
C213 C -1.32406(15) -0.45847(12) 0.92532(9) 0.0200(2) Uani 1 1 d . . . . .
H213 H -1.359364 -0.51645 0.973048 0.024 Uiso 1 1 calc R U . . .
C214 C -1.45229(14) -0.45130(12) 0.84285(9) 0.0208(2) Uani 1 1 d . . . . .
H214 H -1.574854 -0.504313 0.834374 0.025 Uiso 1 1 calc R U . . .
C215 C -1.40068(15) -0.36665(13) 0.77318(9) 0.0205(2) Uani 1 1 d . . . . .
H215 H -1.488095 -0.361259 0.717242 0.025 Uiso 1 1 calc R U . . .
C216 C -1.22119(14) -0.28951(12) 0.78490(8) 0.0169(2) Uani 1 1 d . . . . .
H216 H -1.186475 -0.232261 0.736723 0.02 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
F91 C9 1.3374(12) . ?
F92 C9 1.3397(12) . ?
F93 C9 1.3364(12) . ?
O1 C1 1.2061(13) . ?
O2 C8 1.4091(12) . ?
O2 C3 1.4488(12) . ?
O3 C8 1.4055(12) . ?
O3 C5 1.4502(12) . ?
O11 C1 1.3415(13) . ?
O11 C11 1.4485(14) . ?
C1 C2 1.5109(15) . ?
C2 C3 1.5159(14) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.5216(14) . ?
C3 H3 1 . ?
C4 C5 1.5267(14) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C6 1.5160(14) . ?
C5 H5 1 . ?
C6 C7 1.5353(15) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C111 1.5115(15) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 C211 1.5318(14) . ?
C8 C9 1.5410(14) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C111 C112 1.3936(15) . ?
C111 C116 1.4011(15) . ?
C112 C113 1.3917(17) . ?
C112 H112 0.95 . ?
C113 C114 1.3877(18) . ?
C113 H113 0.95 . ?
C114 C115 1.3930(17) . ?
C114 H114 0.95 . ?
C115 C116 1.3887(15) . ?
C115 H115 0.95 . ?
C116 H116 0.95 . ?
C211 C212 1.3942(14) . ?
C211 C216 1.3973(14) . ?
C212 C213 1.3965(15) . ?
C212 H212 0.95 . ?
C213 C214 1.3937(16) . ?
C213 H213 0.95 . ?
C214 C215 1.3870(17) . ?
C214 H214 0.95 . ?
C215 C216 1.3931(15) . ?
C215 H215 0.95 . ?
C216 H216 0.95 . ?

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
C8 O2 C3 112.13(7) . . ?
C8 O3 C5 113.67(7) . . ?
C1 O11 C11 115.04(9) . . ?
O1 C1 O11 123.75(10) . . ?
O1 C1 C2 124.29(10) . . ?
O11 C1 C2 111.95(9) . . ?
C1 C2 C3 110.72(9) . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C2 105.40(8) . . ?
O2 C3 C4 109.41(8) . . ?
C2 C3 C4 114.45(9) . . ?
O2 C3 H3 109.1 . . ?
C2 C3 H3 109.1 . . ?
C4 C3 H3 109.1 . . ?
C3 C4 C5 108.93(8) . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
O3 C5 C6 106.72(8) . . ?
O3 C5 C4 109.00(8) . . ?
C6 C5 C4 114.16(9) . . ?
O3 C5 H5 108.9 . . ?
C6 C5 H5 108.9 . . ?
C4 C5 H5 108.9 . . ?
C5 C6 C7 112.56(9) . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C111 C7 C6 112.60(9) . . ?
C111 C7 H7A 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C111 C7 H7B 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O3 C8 O2 112.61(8) . . ?
O3 C8 C211 113.51(8) . . ?
O2 C8 C211 112.70(8) . . ?
O3 C8 C9 103.73(8) . . ?
O2 C8 C9 104.08(8) . . ?
C211 C8 C9 109.32(8) . . ?
F93 C9 F91 107.10(8) . . ?
F93 C9 F92 107.55(8) . . ?
F91 C9 F92 107.42(8) . . ?
F93 C9 C8 111.66(8) . . ?
F91 C9 C8 112.19(8) . . ?
F92 C9 C8 110.69(8) . . ?
O11 C11 H11A 109.5 . . ?
O11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O11 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C112 C111 C116 118.09(10) . . ?
C112 C111 C7 121.15(10) . . ?
C116 C111 C7 120.76(9) . . ?
C113 C112 C111 121.16(10) . . ?
C113 C112 H112 119.4 . . ?
C111 C112 H112 119.4 . . ?
C114 C113 C112 120.15(11) . . ?
C114 C113 H113 119.9 . . ?
C112 C113 H113 119.9 . . ?
C113 C114 C115 119.45(11) . . ?
C113 C114 H114 120.3 . . ?
C115 C114 H114 120.3 . . ?
C116 C115 C114 120.21(10) . . ?
C116 C115 H115 119.9 . . ?
C114 C115 H115 119.9 . . ?
C115 C116 C111 120.94(10) . . ?
C115 C116 H116 119.5 . . ?
C111 C116 H116 119.5 . . ?
C212 C211 C216 119.80(9) . . ?
C212 C211 C8 119.94(9) . . ?
C216 C211 C8 120.12(9) . . ?
C211 C212 C213 119.87(10) . . ?
C211 C212 H212 120.1 . . ?
C213 C212 H212 120.1 . . ?
C214 C213 C212 120.16(10) . . ?
C214 C213 H213 119.9 . . ?
C212 C213 H213 119.9 . . ?
C215 C214 C213 119.90(10) . . ?
C215 C214 H214 120 . . ?
C213 C214 H214 120 . . ?
C214 C215 C216 120.27(10) . . ?
C214 C215 H215 119.9 . . ?
C216 C215 H215 119.9 . . ?
C215 C216 C211 120.00(10) . . ?
C215 C216 H216 120 . . ?
C211 C216 H216 120 . . ?

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
C11 O11 C1 O1 1.57(15) . . . . ?
C11 O11 C1 C2 -179.35(9) . . . . ?
O1 C1 C2 C3 -39.59(14) . . . . ?
O11 C1 C2 C3 141.33(9) . . . . ?
C8 O2 C3 C2 179.03(8) . . . . ?
C8 O2 C3 C4 -57.45(10) . . . . ?
C1 C2 C3 O2 -66.25(10) . . . . ?
C1 C2 C3 C4 173.49(8) . . . . ?
O2 C3 C4 C5 55.72(10) . . . . ?
C2 C3 C4 C5 173.73(8) . . . . ?
C8 O3 C5 C6 178.89(8) . . . . ?
C8 O3 C5 C4 55.15(10) . . . . ?
C3 C4 C5 O3 -54.06(10) . . . . ?
C3 C4 C5 C6 -173.27(8) . . . . ?
O3 C5 C6 C7 60.31(11) . . . . ?
C4 C5 C6 C7 -179.21(8) . . . . ?
C5 C6 C7 C111 179.10(8) . . . . ?
C5 O3 C8 O2 -57.00(10) . . . . ?
C5 O3 C8 C211 72.57(10) . . . . ?
C5 O3 C8 C9 -168.90(8) . . . . ?
C3 O2 C8 O3 57.65(10) . . . . ?
C3 O2 C8 C211 -72.33(10) . . . . ?
C3 O2 C8 C9 169.33(8) . . . . ?
O3 C8 C9 F93 178.46(8) . . . . ?
O2 C8 C9 F93 60.47(10) . . . . ?
C211 C8 C9 F93 -60.16(11) . . . . ?
O3 C8 C9 F91 58.21(10) . . . . ?
O2 C8 C9 F91 -59.78(10) . . . . ?
C211 C8 C9 F91 179.59(8) . . . . ?
O3 C8 C9 F92 -61.76(10) . . . . ?
O2 C8 C9 F92 -179.74(8) . . . . ?
C211 C8 C9 F92 59.63(11) . . . . ?
C6 C7 C111 C112 107.31(11) . . . . ?
C6 C7 C111 C116 -71.89(13) . . . . ?
C116 C111 C112 C113 0.62(16) . . . . ?
C7 C111 C112 C113 -178.60(10) . . . . ?
C111 C112 C113 C114 -0.99(18) . . . . ?
C112 C113 C114 C115 0.56(18) . . . . ?
C113 C114 C115 C116 0.22(18) . . . . ?
C114 C115 C116 C111 -0.59(17) . . . . ?
C112 C111 C116 C115 0.16(16) . . . . ?
C7 C111 C116 C115 179.39(10) . . . . ?
O3 C8 C211 C212 -160.64(9) . . . . ?
O2 C8 C211 C212 -31.12(12) . . . . ?
C9 C8 C211 C212 84.10(11) . . . . ?
O3 C8 C211 C216 23.70(13) . . . . ?
O2 C8 C211 C216 153.22(9) . . . . ?
C9 C8 C211 C216 -91.56(11) . . . . ?
C216 C211 C212 C213 0.38(15) . . . . ?
C8 C211 C212 C213 -175.29(9) . . . . ?
C211 C212 C213 C214 -0.42(16) . . . . ?
C212 C213 C214 C215 0.01(17) . . . . ?
C213 C214 C215 C216 0.45(17) . . . . ?
C214 C215 C216 C211 -0.49(17) . . . . ?
C212 C211 C216 C215 0.07(16) . . . . ?
C8 C211 C216 C215 175.74(9) . . . . ?



# SQUEEZE RESULTS (Version = 171016)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.500 151 46 'ethyl acetate/hexane '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL shelx     P -1         R = 0.20
CELL    8.8528   10.3504   14.1556     91.59    107.37    115.30
SPGR P-1
# Solvent Accessible Volume =       152
# Electrons Found in S.A.V. =        46
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.555 1.002 0.490 !      10.31 eA-3
C102 0.428 0.127 0.389 !       8.19 eA-3
C103 0.546 0.088 0.420 !       7.14 eA-3
C104 0.710 0.156 0.388 !       6.58 eA-3
C105 0.559 0.167 0.406 !       5.88 eA-3
Q106 0.594 1.000 0.422 !       0.95 eA-3
Q107 0.671 0.230 0.344 !       0.85 eA-3
C108 0.463 0.037 0.433 !       0.75 eA-3
Q109 0.813 0.184 0.048 !       0.74 eA-3
Q110 0.846 0.819 0.406 !       0.72 eA-3
Q111 0.215 0.412 0.063 !       0.70 eA-3
C112 0.796 0.176 0.451 !       0.69 eA-3
Q113 0.910 0.337 0.284 !       0.69 eA-3
Q114 0.095 0.759 0.190 !       0.68 eA-3
Q115 0.816 0.225 0.013 !       0.66 eA-3
Q116 0.885 0.622 0.387 !       0.64 eA-3
Q117 0.247 0.993 0.021 !       0.63 eA-3
Q118 0.380 0.833 0.225 !       0.63 eA-3
Q119 0.897 0.753 0.356 !       0.62 eA-3
Q120 0.848 0.052 0.179 !       0.62 eA-3
Q121 0.250 0.947 0.067 !       0.62 eA-3
Q122 0.668 0.287 0.165 !       0.62 eA-3
Q123 0.118 0.349 0.091 !       0.61 eA-3
Q124 0.250 0.288 0.483 !       0.61 eA-3
Q125 0.849 0.415 0.096 !       0.60 eA-3
Q126 0.789 0.563 0.457 !       0.60 eA-3
Q127 0.973 0.248 0.124 !       0.58 eA-3
Q128 0.906 0.496 0.133 !       0.58 eA-3
Q129 0.815 0.914 0.160 !       0.57 eA-3
Q130 0.189 0.346 0.499 !       0.57 eA-3
Q131 0.316 0.908 0.158 !       0.57 eA-3
Q132 0.147 0.283 0.177 !       0.57 eA-3
Q133 0.399 0.469 0.123 !       0.56 eA-3
Q134 0.782 0.934 0.086 !       0.56 eA-3
Q135 0.965 0.374 0.250 !       0.56 eA-3
Q136 0.869 0.287 0.136 !       0.54 eA-3
Q137 0.855 0.370 0.147 !       0.53 eA-3
Q138 0.057 0.255 0.131 !       0.53 eA-3
Q139 0.780 0.754 0.472 !       0.52 eA-3
Q140 0.405 0.778 0.264 !       0.52 eA-3
Q141 0.123 0.343 0.046 !       0.51 eA-3
Q142 0.168 0.777 0.193 !       0.51 eA-3
Q143 0.877 0.159 0.152 !       0.50 eA-3
;

# END of CIF
####################################################################### 
# 
# 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_2016gu0009_0m
_database_code_depnum_ccdc_archive 'CCDC 1511482'
_audit_update_record             
;
2016-10-25 deposited with the CCDC.
2016-11-23 downloaded from the CCDC.
;
_audit_creation_date             2016-06-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 F3 N O5'
_chemical_formula_sum            'C23 H24 F3 N O5'
_chemical_formula_weight         451.43
_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'
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'
F F 0.0171 0.0103 '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                   8.898(3)
_cell_length_b                   26.042(7)
_cell_length_c                   9.427(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.704(6)
_cell_angle_gamma                90
_cell_volume                     2183.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2565
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.17
_cell_measurement_theta_min      2.29
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.954
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.4486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1485 before and 0.1092 after correction.
The Ratio of minimum to maximum transmission is 0.6020.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1173
_diffrn_reflns_av_unetI/netI     0.1185
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12762
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.277
_diffrn_reflns_theta_max         25.277
_diffrn_reflns_theta_min         1.564
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2472
_reflns_number_total             3903
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1229
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.036
_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)+(0.0890P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1978
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6'(H6'), C2(H2), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C7'(H7'A,H7'B), C5'(H5'A,H5'B), C8'(H8'A,H8'B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C14(H14), C10(H10), C12(H12), C10'(H10'), C12'(H12'), C4(H4),
 C14'(H14'), C11'(H11'), C13(H13), C11(H11), C13'(H13')
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_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
F2 F 0.6276(3) 0.44084(8) 0.6640(2) 0.0298(6) Uani 1 1 d . . . . .
F1 F 0.6004(3) 0.36064(8) 0.7041(2) 0.0297(6) Uani 1 1 d . . . . .
F3 F 0.8081(3) 0.38874(9) 0.6278(2) 0.0331(6) Uani 1 1 d . . . . .
O3' O 0.6440(3) 0.33565(9) 0.4342(2) 0.0203(6) Uani 1 1 d . . . . .
O1' O 0.6814(3) 0.42287(9) 0.3876(2) 0.0211(6) Uani 1 1 d . . . . .
O7 O 0.4463(3) 0.23346(10) 0.2755(3) 0.0268(7) Uani 1 1 d . . . . .
O5 O 0.9575(3) 0.24270(11) 0.1392(3) 0.0311(7) Uani 1 1 d . . . . .
O6 O 0.5963(3) 0.21087(10) 0.4580(3) 0.0296(7) Uani 1 1 d . . . . .
N3 N 0.8348(4) 0.25951(12) 0.3422(3) 0.0248(8) Uani 1 1 d . . . . .
H3 H 0.8461 0.2627 0.4327 0.030 Uiso 1 1 calc R . . . .
C1 C 0.5749(5) 0.23375(14) 0.3490(4) 0.0218(9) Uani 1 1 d . . . . .
C9 C 0.4326(5) 0.39370(14) 0.4531(4) 0.0209(9) Uani 1 1 d . . . . .
C15 C 0.6601(5) 0.39424(14) 0.6152(4) 0.0232(9) Uani 1 1 d . . . . .
C2' C 0.6009(5) 0.38611(13) 0.4644(4) 0.0207(9) Uani 1 1 d . . . . .
C9' C 0.7719(5) 0.55260(14) 0.1168(4) 0.0241(9) Uani 1 1 d . . . . .
C14 C 0.3720(5) 0.44111(15) 0.4212(4) 0.0252(9) Uani 1 1 d . . . . .
H14 H 0.4352 0.4686 0.4033 0.030 Uiso 1 1 calc R . . . .
C10 C 0.3374(5) 0.35290(15) 0.4819(4) 0.0254(9) Uani 1 1 d . . . . .
H10 H 0.3774 0.3208 0.5037 0.031 Uiso 1 1 calc R . . . .
C6' C 0.6768(5) 0.41421(14) 0.2357(4) 0.0226(9) Uani 1 1 d . . . . .
H6' H 0.5721 0.4164 0.2009 0.027 Uiso 1 1 calc R . . . .
C7' C 0.7655(5) 0.45696(14) 0.1694(4) 0.0245(9) Uani 1 1 d . . . . .
H7'A H 0.7686 0.4513 0.0678 0.029 Uiso 1 1 calc R . . . .
H7'B H 0.8680 0.4561 0.2073 0.029 Uiso 1 1 calc R . . . .
C5' C 0.7348(5) 0.36100(14) 0.2075(4) 0.0227(9) Uani 1 1 d . . . . .
H5'A H 0.8388 0.3581 0.2402 0.027 Uiso 1 1 calc R . . . .
H5'B H 0.7294 0.3539 0.1065 0.027 Uiso 1 1 calc R . . . .
C2 C 0.6883(5) 0.26744(14) 0.2785(4) 0.0217(9) Uani 1 1 d . . . . .
H2 H 0.6917 0.2575 0.1783 0.026 Uiso 1 1 calc R . . . .
C4' C 0.6389(5) 0.32332(13) 0.2857(4) 0.0216(9) Uani 1 1 d . . . . .
H4' H 0.5348 0.3261 0.2495 0.026 Uiso 1 1 calc R . . . .
C12 C 0.1243(5) 0.40765(16) 0.4442(4) 0.0296(10) Uani 1 1 d . . . . .
H12 H 0.0206 0.4123 0.4408 0.036 Uiso 1 1 calc R . . . .
C8' C 0.6988(5) 0.50975(14) 0.1966(4) 0.0264(9) Uani 1 1 d . . . . .
H8'A H 0.5926 0.5090 0.1705 0.032 Uiso 1 1 calc R . . . .
H8'B H 0.7077 0.5170 0.2974 0.032 Uiso 1 1 calc R . . . .
C10' C 0.9007(5) 0.57553(15) 0.1677(4) 0.0275(10) Uani 1 1 d . . . . .
H10' H 0.9450 0.5640 0.2524 0.033 Uiso 1 1 calc R . . . .
C12' C 0.9024(5) 0.63281(14) -0.0294(4) 0.0280(10) Uani 1 1 d . . . . .
H12' H 0.9452 0.6600 -0.0778 0.034 Uiso 1 1 calc R . . . .
C4 C 0.9533(5) 0.24745(14) 0.2676(4) 0.0266(10) Uani 1 1 d . . . . .
H4 H 1.0430 0.2420 0.3186 0.032 Uiso 1 1 calc R . . . .
C14' C 0.7110(5) 0.56995(15) -0.0105(4) 0.0293(10) Uani 1 1 d . . . . .
H14' H 0.6248 0.5544 -0.0485 0.035 Uiso 1 1 calc R . . . .
C11' C 0.9669(5) 0.61569(15) 0.0954(4) 0.0294(10) Uani 1 1 d . . . . .
H11' H 1.0546 0.6308 0.1315 0.035 Uiso 1 1 calc R . . . .
C13 C 0.2179(5) 0.44811(15) 0.4155(4) 0.0279(10) Uani 1 1 d . . . . .
H13 H 0.1777 0.4801 0.3924 0.033 Uiso 1 1 calc R . . . .
C11 C 0.1845(5) 0.35999(16) 0.4780(4) 0.0271(10) Uani 1 1 d . . . . .
H11 H 0.1211 0.3327 0.4983 0.032 Uiso 1 1 calc R . . . .
C13' C 0.7754(5) 0.60991(15) -0.0823(4) 0.0298(10) Uani 1 1 d . . . . .
H13' H 0.7318 0.6213 -0.1675 0.036 Uiso 1 1 calc R . . . .
C8 C 0.3299(5) 0.20227(16) 0.3345(5) 0.0354(11) Uani 1 1 d . . . . .
H8A H 0.2467 0.1998 0.2677 0.053 Uiso 1 1 calc GR . . . .
H8B H 0.2969 0.2177 0.4207 0.053 Uiso 1 1 calc GR . . . .
H8C H 0.3687 0.1685 0.3544 0.053 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
F2 C15 1.333(4) . ?
F1 C15 1.333(4) . ?
F3 C15 1.326(5) . ?
O3' C2' 1.401(4) . ?
O3' C4' 1.436(4) . ?
O1' C2' 1.409(4) . ?
O1' C6' 1.449(4) . ?
O7 C1 1.320(5) . ?
O7 C8 1.440(5) . ?
O5 C4 1.218(5) . ?
O6 C1 1.198(4) . ?
N3 H3 0.8600 . ?
N3 C2 1.434(5) . ?
N3 C4 1.322(5) . ?
C1 C2 1.507(6) . ?
C9 C2' 1.511(6) . ?
C9 C14 1.377(5) . ?
C9 C10 1.391(6) . ?
C15 C2' 1.515(5) . ?
C9' C8' 1.504(5) . ?
C9' C10' 1.366(6) . ?
C9' C14' 1.378(5) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(6) . ?
C6' H6' 0.9800 . ?
C6' C7' 1.511(5) . ?
C6' C5' 1.505(5) . ?
C7' H7'A 0.9700 . ?
C7' H7'B 0.9700 . ?
C7' C8' 1.522(5) . ?
C5' H5'A 0.9700 . ?
C5' H5'B 0.9700 . ?
C5' C4' 1.507(5) . ?
C2 H2 0.9800 . ?
C2 C4' 1.522(5) . ?
C4' H4' 0.9800 . ?
C12 H12 0.9300 . ?
C12 C13 1.375(6) . ?
C12 C11 1.385(6) . ?
C8' H8'A 0.9700 . ?
C8' H8'B 0.9700 . ?
C10' H10' 0.9300 . ?
C10' C11' 1.389(6) . ?
C12' H12' 0.9300 . ?
C12' C11' 1.368(6) . ?
C12' C13' 1.360(6) . ?
C4 H4 0.9300 . ?
C14' H14' 0.9300 . ?
C14' C13' 1.376(6) . ?
C11' H11' 0.9300 . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C13' H13' 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C2' O3' C4' 114.0(3) . . ?
C2' O1' C6' 113.7(3) . . ?
C1 O7 C8 115.0(3) . . ?
C2 N3 H3 118.6 . . ?
C4 N3 H3 118.6 . . ?
C4 N3 C2 122.7(3) . . ?
O7 C1 C2 110.7(3) . . ?
O6 C1 O7 124.1(4) . . ?
O6 C1 C2 125.2(4) . . ?
C14 C9 C2' 120.9(3) . . ?
C14 C9 C10 119.4(4) . . ?
C10 C9 C2' 119.6(3) . . ?
F2 C15 C2' 112.2(3) . . ?
F1 C15 F2 106.6(3) . . ?
F1 C15 C2' 111.4(3) . . ?
F3 C15 F2 107.0(3) . . ?
F3 C15 F1 106.6(3) . . ?
F3 C15 C2' 112.6(3) . . ?
O3' C2' O1' 112.8(3) . . ?
O3' C2' C9 112.6(3) . . ?
O3' C2' C15 103.4(3) . . ?
O1' C2' C9 113.1(3) . . ?
O1' C2' C15 102.7(3) . . ?
C9 C2' C15 111.3(3) . . ?
C10' C9' C8' 121.3(3) . . ?
C10' C9' C14' 117.8(4) . . ?
C14' C9' C8' 120.9(4) . . ?
C9 C14 H14 119.7 . . ?
C9 C14 C13 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(4) . . ?
C11 C10 H10 120.0 . . ?
O1' C6' H6' 108.7 . . ?
O1' C6' C7' 107.1(3) . . ?
O1' C6' C5' 108.6(3) . . ?
C7' C6' H6' 108.7 . . ?
C5' C6' H6' 108.7 . . ?
C5' C6' C7' 114.8(3) . . ?
C6' C7' H7'A 109.1 . . ?
C6' C7' H7'B 109.1 . . ?
C6' C7' C8' 112.6(3) . . ?
H7'A C7' H7'B 107.8 . . ?
C8' C7' H7'A 109.1 . . ?
C8' C7' H7'B 109.1 . . ?
C6' C5' H5'A 110.1 . . ?
C6' C5' H5'B 110.1 . . ?
C6' C5' C4' 108.1(3) . . ?
H5'A C5' H5'B 108.4 . . ?
C4' C5' H5'A 110.1 . . ?
C4' C5' H5'B 110.1 . . ?
N3 C2 C1 110.1(3) . . ?
N3 C2 H2 108.2 . . ?
N3 C2 C4' 112.3(3) . . ?
C1 C2 H2 108.2 . . ?
C1 C2 C4' 109.8(3) . . ?
C4' C2 H2 108.2 . . ?
O3' C4' C5' 109.2(3) . . ?
O3' C4' C2 104.9(3) . . ?
O3' C4' H4' 109.0 . . ?
C5' C4' C2 115.6(3) . . ?
C5' C4' H4' 109.0 . . ?
C2 C4' H4' 109.0 . . ?
C13 C12 H12 120.0 . . ?
C13 C12 C11 120.0(4) . . ?
C11 C12 H12 120.0 . . ?
C9' C8' C7' 114.2(3) . . ?
C9' C8' H8'A 108.7 . . ?
C9' C8' H8'B 108.7 . . ?
C7' C8' H8'A 108.7 . . ?
C7' C8' H8'B 108.7 . . ?
H8'A C8' H8'B 107.6 . . ?
C9' C10' H10' 119.3 . . ?
C9' C10' C11' 121.4(4) . . ?
C11' C10' H10' 119.3 . . ?
C11' C12' H12' 120.1 . . ?
C13' C12' H12' 120.1 . . ?
C13' C12' C11' 119.7(4) . . ?
O5 C4 N3 126.9(4) . . ?
O5 C4 H4 116.5 . . ?
N3 C4 H4 116.5 . . ?
C9' C14' H14' 119.4 . . ?
C13' C14' C9' 121.2(4) . . ?
C13' C14' H14' 119.4 . . ?
C10' C11' H11' 120.2 . . ?
C12' C11' C10' 119.6(4) . . ?
C12' C11' H11' 120.2 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.8(4) . . ?
C12 C13 H13 120.1 . . ?
C10 C11 C12 120.2(4) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C12' C13' C14' 120.3(4) . . ?
C12' C13' H13' 119.8 . . ?
C14' C13' H13' 119.8 . . ?
O7 C8 H8A 109.5 . . ?
O7 C8 H8B 109.5 . . ?
O7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
F2 C15 C2' O3' -179.2(3) . . . . ?
F2 C15 C2' O1' 63.3(4) . . . . ?
F2 C15 C2' C9 -58.0(4) . . . . ?
F1 C15 C2' O3' -59.8(4) . . . . ?
F1 C15 C2' O1' -177.2(3) . . . . ?
F1 C15 C2' C9 61.5(4) . . . . ?
F3 C15 C2' O3' 60.0(4) . . . . ?
F3 C15 C2' O1' -57.5(4) . . . . ?
F3 C15 C2' C9 -178.8(3) . . . . ?
O1' C6' C7' C8' -61.5(4) . . . . ?
O1' C6' C5' C4' 57.7(4) . . . . ?
O7 C1 C2 N3 -168.4(3) . . . . ?
O7 C1 C2 C4' 67.4(4) . . . . ?
O6 C1 C2 N3 12.7(5) . . . . ?
O6 C1 C2 C4' -111.4(4) . . . . ?
N3 C2 C4' O3' -57.9(4) . . . . ?
N3 C2 C4' C5' 62.5(4) . . . . ?
C1 C2 C4' O3' 65.0(4) . . . . ?
C1 C2 C4' C5' -174.7(3) . . . . ?
C9 C14 C13 C12 1.0(6) . . . . ?
C9 C10 C11 C12 0.6(6) . . . . ?
C2' O3' C4' C5' 55.9(4) . . . . ?
C2' O3' C4' C2 -179.6(3) . . . . ?
C2' O1' C6' C7' 179.2(3) . . . . ?
C2' O1' C6' C5' -56.4(4) . . . . ?
C2' C9 C14 C13 -177.9(3) . . . . ?
C2' C9 C10 C11 177.1(3) . . . . ?
C9' C10' C11' C12' 0.0(6) . . . . ?
C9' C14' C13' C12' 0.8(7) . . . . ?
C14 C9 C2' O3' -153.2(3) . . . . ?
C14 C9 C2' O1' -23.9(5) . . . . ?
C14 C9 C2' C15 91.1(4) . . . . ?
C14 C9 C10 C11 0.2(5) . . . . ?
C10 C9 C2' O3' 29.9(5) . . . . ?
C10 C9 C2' O1' 159.2(3) . . . . ?
C10 C9 C2' C15 -85.8(4) . . . . ?
C10 C9 C14 C13 -1.0(5) . . . . ?
C6' O1' C2' O3' 53.4(4) . . . . ?
C6' O1' C2' C9 -75.8(4) . . . . ?
C6' O1' C2' C15 164.1(3) . . . . ?
C6' C7' C8' C9' -172.5(3) . . . . ?
C6' C5' C4' O3' -57.7(4) . . . . ?
C6' C5' C4' C2 -175.6(3) . . . . ?
C7' C6' C5' C4' 177.5(3) . . . . ?
C5' C6' C7' C8' 177.9(3) . . . . ?
C2 N3 C4 O5 1.9(6) . . . . ?
C4' O3' C2' O1' -53.2(4) . . . . ?
C4' O3' C2' C9 76.3(4) . . . . ?
C4' O3' C2' C15 -163.4(3) . . . . ?
C8' C9' C10' C11' -178.9(4) . . . . ?
C8' C9' C14' C13' 178.5(4) . . . . ?
C10' C9' C8' C7' -83.7(5) . . . . ?
C10' C9' C14' C13' -1.7(6) . . . . ?
C4 N3 C2 C1 126.1(4) . . . . ?
C4 N3 C2 C4' -111.2(4) . . . . ?
C14' C9' C8' C7' 96.2(5) . . . . ?
C14' C9' C10' C11' 1.3(6) . . . . ?
C11' C12' C13' C14' 0.5(7) . . . . ?
C13 C12 C11 C10 -0.6(6) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C13' C12' C11' C10' -0.9(6) . . . . ?
C8 O7 C1 O6 -1.1(5) . . . . ?
C8 O7 C1 C2 -179.9(3) . . . . ?

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