# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_a20180274_as552
_database_code_depnum_ccdc_archive 'CCDC 1989940'
loop_
_audit_author_name
_audit_author_address
'Leire Sanfelices'
;University of the Basque Country, Bilbao, Spain
Spain
;
_audit_update_record             
;
2020-03-12 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2020-02-11T11:42:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C20 H13 F3 O'
_chemical_formula_sum            'C20 H13 F3 O'
_chemical_formula_weight         326.3

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.5329(2)
_cell_length_b                   17.6088(2)
_cell_length_c                   9.47700(11)
_cell_angle_alpha                90
_cell_angle_beta                 102.1749(12)
_cell_angle_gamma                90
_cell_volume                     3023.18(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    7218
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      74.291

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

_exptl_crystal_density_diffrn    1.434
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.260
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_F_000             1344
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1418
9 -7 1 0.1482
3 -2 -6 0.2013
-9 7 -1 0.1662
0 -6 5 0.1860
8 8 1 0.1214
1 7 -5 0.2059
-8 -8 -1 0.1385

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

_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.875
_exptl_absorpt_correction_T_max  1

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

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.0705629
_diffrn_orient_matrix_ub_12      0.0389783
_diffrn_orient_matrix_ub_13      -0.0255561
_diffrn_orient_matrix_ub_21      -0.0253944
_diffrn_orient_matrix_ub_22      0.0755261
_diffrn_orient_matrix_ub_23      0.0557085
_diffrn_orient_matrix_ub_31      0.0400979
_diffrn_orient_matrix_ub_32      -0.0207956
_diffrn_orient_matrix_ub_33      0.1545614
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_number            10049
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.5
_diffrn_reflns_theta_max         68.982
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             2784
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      8.00  34.00   1.00    1.00    --  -42.13  77.00 150.00   26
  2  ω    -68.00 -38.00   1.00    1.00    --  -42.13  77.00 150.00   30
  3  ω      5.00  67.00   1.00    1.00    --   42.13-125.00  60.00   62
  4  ω     20.00 115.00   1.00    1.00    --   42.13  57.00  60.00   95
  5  ω     26.00  71.00   1.00    1.00    --   42.13  38.00 -90.00   45
  6  ω     18.00 112.00   1.00    1.00    --   42.13  38.00-180.00   94
  7  ω     86.00 149.00   1.00    1.00    --  107.93  45.00-180.00   63
  8  ω     36.00  65.00   1.00    1.00    --  107.93 -30.00  90.00   29
  9  ω     32.00  69.00   1.00    1.00    --  107.93 -30.00-120.00   37
 10  ω     35.00 114.00   1.00    1.00    --  107.93-125.00  60.00   79
 11  ω     34.00  64.00   1.00    1.00    --  107.93 -30.00 150.00   30
 12  ω     44.00  70.00   1.00    1.00    --  107.93-125.00 -60.00   26
 13  ω     92.00 117.00   1.00    1.00    --  107.93-125.00 -60.00   25
 14  ω     86.00 129.00   1.00    1.00    --  107.93 -77.00   0.00   43
 15  ω     38.00 127.00   1.00    1.00    --  107.93 -77.00-180.00   89
 16  ω     40.00  67.00   1.00    1.00    --  107.93 -30.00   0.00   27
 17  ω    110.00 157.00   1.00    1.00    --  107.93  45.00-150.00   47
 18  ω     32.00  60.00   1.00    1.00    --  107.93 -30.00-180.00   28
 19  ω     36.00  68.00   1.00    1.00    --  107.93 -30.00 120.00   32
 20  ω     35.00  67.00   1.00    1.00    --  107.93 -30.00  60.00   32
 21  ω     27.00  86.00   1.00    1.00    --  107.93 -94.00 -30.00   59
 22  ω     58.00 114.00   1.00    1.00    --  107.93-125.00-180.00   56
 23  ω     78.00 145.00   1.00    1.00    --  107.93 125.00-150.00   67
 24  ω     36.00  65.00   1.00    1.00    --  107.93 -45.00   0.00   29
;

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 shelx_SHELXL_version_number            2018/3

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²+2.2739P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     253
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.111
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_restrained_S_all      1.206
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.039

#----------------------------------------------------------------------------#
#                   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
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.41959(19) -0.05786(18) 0.0888(5) 0.0533(8) Uani 0.679(9) 1 d . U P A 1
F1B F 0.4254(4) -0.0482(4) 0.1356(6) 0.0370(12) Uani 0.321(9) 1 d . U P A 2
F2 F 0.38498(11) 0.0190(3) -0.0865(2) 0.0545(8) Uani 0.679(9) 1 d . U P A 1
F2B F 0.4188(4) 0.0673(4) 0.0707(9) 0.0509(14) Uani 0.321(9) 1 d . U P A 2
F3 F 0.42698(14) 0.06346(17) 0.1242(4) 0.0469(7) Uani 0.679(9) 1 d . U P A 1
F3B F 0.3830(3) -0.0193(5) -0.0851(5) 0.0561(14) Uani 0.321(9) 1 d . U P A 2
O1 O 0.04948(5) 0.07756(6) 0.08857(11) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.08904(8) 0.01447(8) 0.16462(16) 0.0310(3) Uani 1 1 d . . . . .
H1A H 0.061799 -0.033133 0.133965 0.037 Uiso 1 1 calc R . . . .
H1B H 0.09226 0.020823 0.269559 0.037 Uiso 1 1 calc R . . . .
C2 C 0.16592(8) 0.00880(8) 0.13536(14) 0.0272(3) Uani 1 1 d . . . . .
C3 C 0.19977(8) -0.06092(8) 0.11851(14) 0.0283(3) Uani 1 1 d . . . . .
C4 C 0.27063(8) -0.05996(8) 0.08915(15) 0.0313(3) Uani 1 1 d . . . . .
H4 H 0.2936(9) -0.1062(10) 0.0764(18) 0.033(4) Uiso 1 1 d . . . . .
C5 C 0.30742(8) 0.00775(8) 0.08043(16) 0.0313(3) Uani 1 1 d . . . . .
C6 C 0.27406(8) 0.07649(8) 0.09670(15) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.2979(10) 0.1222(10) 0.0883(18) 0.035(4) Uiso 1 1 d . . . . .
C7 C 0.20282(8) 0.07738(8) 0.12402(14) 0.0274(3) Uani 1 1 d . . . . .
C8 C 0.16303(8) 0.14898(8) 0.13514(13) 0.0272(3) Uani 1 1 d . . . . .
C9 C 0.19641(8) 0.22051(8) 0.15588(14) 0.0305(3) Uani 1 1 d . . . . .
H9 H 0.248597 0.224361 0.170758 0.037 Uiso 1 1 calc R . . . .
C10 C 0.15475(9) 0.28567(8) 0.15510(15) 0.0329(3) Uani 1 1 d . . . . .
H10 H 0.178336 0.333804 0.169118 0.039 Uiso 1 1 calc R . . . .
C11 C 0.07830(9) 0.28080(9) 0.13379(15) 0.0346(3) Uani 1 1 d . . . . .
H11 H 0.049668 0.325596 0.133098 0.042 Uiso 1 1 calc R . . . .
C12 C 0.04400(8) 0.21072(9) 0.11361(15) 0.0332(3) Uani 1 1 d . . . . .
H12 H -0.008221 0.207205 0.098514 0.04 Uiso 1 1 calc R . . . .
C13 C 0.08622(8) 0.14571(8) 0.11555(14) 0.0287(3) Uani 1 1 d . . . . .
C14 C 0.16444(7) -0.13566(8) 0.13229(14) 0.0279(3) Uani 1 1 d . . . . .
C15 C 0.13152(8) -0.15198(8) 0.24867(14) 0.0308(3) Uani 1 1 d . . . . .
H15 H 0.130478 -0.114163 0.319717 0.037 Uiso 1 1 calc R . . . .
C16 C 0.10042(8) -0.22242(9) 0.26193(16) 0.0344(3) Uani 1 1 d . . . . .
H16 H 0.078528 -0.232619 0.342001 0.041 Uiso 1 1 calc R . . . .
C17 C 0.10108(8) -0.27816(9) 0.15880(17) 0.0349(3) Uani 1 1 d . . . . .
H17 H 0.079375 -0.326368 0.167257 0.042 Uiso 1 1 calc R . . . .
C18 C 0.13383(8) -0.26266(8) 0.04316(16) 0.0337(3) Uani 1 1 d . . . . .
H18 H 0.134584 -0.300587 -0.027804 0.04 Uiso 1 1 calc R . . . .
C19 C 0.16543(8) -0.19244(8) 0.03015(15) 0.0307(3) Uani 1 1 d . . . . .
H19 H 0.188029 -0.182848 -0.049215 0.037 Uiso 1 1 calc R . . . .
C20 C 0.38406(9) 0.00621(9) 0.05179(18) 0.0367(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
F1 C20 1.316(3) . ?
F1B C20 1.370(6) . ?
F2 C20 1.333(3) . ?
F2B C20 1.248(7) . ?
F3 C20 1.374(3) . ?
F3B C20 1.369(5) . ?
O1 C1 1.4382(17) . ?
O1 C13 1.3768(17) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C1 C2 1.511(2) . ?
C2 C3 1.4030(19) . ?
C2 C7 1.4031(19) . ?
C3 C4 1.399(2) . ?
C3 C14 1.4879(19) . ?
C4 H4 0.938(17) . ?
C4 C5 1.385(2) . ?
C5 C6 1.383(2) . ?
C5 C20 1.501(2) . ?
C6 H6 0.930(18) . ?
C6 C7 1.398(2) . ?
C7 C8 1.4756(19) . ?
C8 C9 1.399(2) . ?
C8 C13 1.397(2) . ?
C9 H9 0.95 . ?
C9 C10 1.382(2) . ?
C10 H10 0.95 . ?
C10 C11 1.391(2) . ?
C11 H11 0.95 . ?
C11 C12 1.383(2) . ?
C12 H12 0.95 . ?
C12 C13 1.385(2) . ?
C14 C15 1.3983(19) . ?
C14 C19 1.394(2) . ?
C15 H15 0.95 . ?
C15 C16 1.385(2) . ?
C16 H16 0.95 . ?
C16 C17 1.387(2) . ?
C17 H17 0.95 . ?
C17 C18 1.387(2) . ?
C18 H18 0.95 . ?
C18 C19 1.385(2) . ?
C19 H19 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
C13 O1 C1 113.60(11) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.09(11) . . ?
H1A C1 H1B 108 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C3 C2 C1 122.70(12) . . ?
C3 C2 C7 120.50(13) . . ?
C7 C2 C1 116.79(12) . . ?
C2 C3 C14 123.25(12) . . ?
C4 C3 C2 118.24(13) . . ?
C4 C3 C14 118.50(12) . . ?
C3 C4 H4 119.0(10) . . ?
C5 C4 C3 121.14(13) . . ?
C5 C4 H4 119.8(10) . . ?
C4 C5 C20 119.46(13) . . ?
C6 C5 C4 120.65(14) . . ?
C6 C5 C20 119.88(13) . . ?
C5 C6 H6 121.1(10) . . ?
C5 C6 C7 119.51(14) . . ?
C7 C6 H6 119.4(10) . . ?
C2 C7 C8 118.09(12) . . ?
C6 C7 C2 119.94(13) . . ?
C6 C7 C8 121.91(13) . . ?
C9 C8 C7 124.50(12) . . ?
C13 C8 C7 117.76(12) . . ?
C13 C8 C9 117.63(13) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.12(13) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120 . . ?
C9 C10 C11 120.01(14) . . ?
C11 C10 H10 120 . . ?
C10 C11 H11 120 . . ?
C12 C11 C10 119.98(13) . . ?
C12 C11 H11 120 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.60(13) . . ?
C13 C12 H12 120.2 . . ?
O1 C13 C8 120.71(12) . . ?
O1 C13 C12 117.52(12) . . ?
C12 C13 C8 121.65(13) . . ?
C15 C14 C3 121.62(12) . . ?
C19 C14 C3 120.19(12) . . ?
C19 C14 C15 118.17(13) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.99(13) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.28(13) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.20(14) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.65(13) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.6 . . ?
C18 C19 C14 120.71(13) . . ?
C18 C19 H19 119.6 . . ?
F1 C20 F2 107.29(19) . . ?
F1 C20 F3 107.0(2) . . ?
F1 C20 C5 113.98(19) . . ?
F1B C20 C5 110.0(3) . . ?
F2 C20 F3 103.92(18) . . ?
F2 C20 C5 112.53(15) . . ?
F2B C20 F1B 108.1(4) . . ?
F2B C20 F3B 108.8(3) . . ?
F2B C20 C5 116.0(3) . . ?
F3 C20 C5 111.50(16) . . ?
F3B C20 F1B 102.4(3) . . ?
F3B C20 C5 110.7(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
O1 C1 C2 C3 -141.85(13) . . . . ?
O1 C1 C2 C7 37.55(17) . . . . ?
C1 O1 C13 C8 36.10(17) . . . . ?
C1 O1 C13 C12 -147.75(12) . . . . ?
C1 C2 C3 C4 178.88(13) . . . . ?
C1 C2 C3 C14 -2.0(2) . . . . ?
C1 C2 C7 C6 -179.84(12) . . . . ?
C1 C2 C7 C8 -2.55(18) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C2 C3 C14 C15 -47.89(19) . . . . ?
C2 C3 C14 C19 134.02(14) . . . . ?
C2 C7 C8 C9 166.13(12) . . . . ?
C2 C7 C8 C13 -17.64(18) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C3 C2 C7 C8 176.85(11) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C3 C4 C5 C20 178.72(14) . . . . ?
C3 C14 C15 C16 -178.43(13) . . . . ?
C3 C14 C19 C18 178.90(12) . . . . ?
C4 C3 C14 C15 131.25(14) . . . . ?
C4 C3 C14 C19 -46.84(18) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C4 C5 C20 F1 -23.6(3) . . . . ?
C4 C5 C20 F1B -44.6(3) . . . . ?
C4 C5 C20 F2 98.9(3) . . . . ?
C4 C5 C20 F2B -167.6(4) . . . . ?
C4 C5 C20 F3 -144.8(2) . . . . ?
C4 C5 C20 F3B 67.8(4) . . . . ?
C5 C6 C7 C2 0.3(2) . . . . ?
C5 C6 C7 C8 -176.89(12) . . . . ?
C6 C5 C20 F1 156.9(3) . . . . ?
C6 C5 C20 F1B 135.9(3) . . . . ?
C6 C5 C20 F2 -80.6(3) . . . . ?
C6 C5 C20 F2B 12.9(5) . . . . ?
C6 C5 C20 F3 35.7(3) . . . . ?
C6 C5 C20 F3B -111.7(4) . . . . ?
C6 C7 C8 C9 -16.6(2) . . . . ?
C6 C7 C8 C13 159.59(13) . . . . ?
C7 C2 C3 C4 -0.5(2) . . . . ?
C7 C2 C3 C14 178.65(12) . . . . ?
C7 C8 C9 C10 175.40(12) . . . . ?
C7 C8 C13 O1 0.78(18) . . . . ?
C7 C8 C13 C12 -175.21(12) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C9 C8 C13 O1 177.27(12) . . . . ?
C9 C8 C13 C12 1.28(19) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 O1 -177.16(12) . . . . ?
C11 C12 C13 C8 -1.1(2) . . . . ?
C13 O1 C1 C2 -54.13(15) . . . . ?
C13 C8 C9 C10 -0.83(19) . . . . ?
C14 C3 C4 C5 -177.58(12) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C14 C19 C18 0.8(2) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C14 -0.6(2) . . . . ?
C19 C14 C15 C16 -0.3(2) . . . . ?
C20 C5 C6 C7 -179.69(13) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# 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_a20180220_as551
_database_code_depnum_ccdc_archive 'CCDC 1989936'
loop_
_audit_author_name
_audit_author_address
'Leire Sanelices'
;University of the Basque Country, Bilbao, Spain
Spain
;
_audit_update_record             
;
2020-03-12 deposited with the CCDC.	2021-07-21 downloaded from the CCDC.
;

_audit_creation_date             2020-02-10T16:04:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_formula_moiety         'C22 H17 F3 O'
_chemical_formula_sum            'C22 H17 F3 O'
_chemical_formula_weight         354.35

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7235(4)
_cell_length_b                   9.8806(3)
_cell_length_c                   10.7952(4)
_cell_angle_alpha                99.278(3)
_cell_angle_beta                 94.538(3)
_cell_angle_gamma                113.082(3)
_cell_volume                     834.34(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.01(10)
_cell_measurement_reflns_used    4689
_cell_measurement_theta_min      4.962
_cell_measurement_theta_max      74.326

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

_exptl_crystal_size_max          0.698
_exptl_crystal_size_mid          0.415
_exptl_crystal_size_min          0.336
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             368
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 7 0.1689
-1 6 1 0.2311
0 1 -1 0.3023
2 -5 -3 0.1598
1 -6 -1 0.2261
5 -1 0 0.1558
1 5 0 0.2508
-1 0 0 0.1468
1 -1 -3 0.2532
-2 4 5 0.2202


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


_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_T_max  0.786
#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_ambient_temperature      150.01(10)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'Multilayer optics'
_diffrn_source_voltage           50
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_radiation_probe          x-ray
_diffrn_detector_area_resol_mean 5.2012
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_ub_11      0.1445279
_diffrn_orient_matrix_ub_12      0.0235626
_diffrn_orient_matrix_ub_13      0.1043515
_diffrn_orient_matrix_ub_21      -0.1258945
_diffrn_orient_matrix_ub_22      -0.0402548
_diffrn_orient_matrix_ub_23      0.0946068
_diffrn_orient_matrix_ub_31      -0.0322835
_diffrn_orient_matrix_ub_32      -0.1669436
_diffrn_orient_matrix_ub_33      -0.0399505
_diffrn_measurement_device       'four-circleκ-geometry diffractometer'
_diffrn_measurement_device_type  'Agilent SuperNova'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_number            5454
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.976
_diffrn_reflns_theta_max         68.996
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_coverage         0
_reflns_number_total             3047
_reflns_number_gt                2879
_reflns_threshold_expression     'I > 2σ(I)'
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -32.00   1.00    1.00    --  -42.13  38.00 -30.00   30
  2  ω    -30.00  -3.00   1.00    1.00    --  -42.13  38.00 -30.00   27
  3  ω     18.00 112.00   1.00    1.00    --   42.13  38.00 150.00   94
  4  ω    -32.00  63.00   1.00    1.00    --   42.13 -38.00 -30.00   95
  5  ω      5.00  97.00   1.00    1.00    --   42.13-125.00 -90.00   92
  6  ω     36.00  68.00   1.00    1.00    --  107.93 -45.00  30.00   32
  7  ω     32.00  61.00   1.00    1.00    --  107.93 -30.00 -60.00   29
  8  ω     35.00  63.00   1.00    1.00    --  107.93 -45.00  90.00   28
  9  ω     50.00  76.00   1.00    1.00    --  107.93 -45.00-180.00   26
 10  ω     37.00 104.00   1.00    1.00    --  107.93-125.00 150.00   67
 11  ω    107.00 134.00   1.00    1.00    --  107.93 -77.00-180.00   27
 12  ω     38.00  65.00   1.00    1.00    --  107.93 -45.00   0.00   27
 13  ω     38.00  65.00   1.00    1.00    --  107.93 -30.00-150.00   27
 14  ω     30.00  94.00   1.00    1.00    --  107.93 -94.00  30.00   64
 15  ω     36.00 118.00   1.00    1.00    --  107.93-125.00-150.00   82
 16  ω     32.00  65.00   1.00    1.00    --  107.93 -77.00-180.00   33
 17  ω     35.00  85.00   1.00    1.00    --  107.93-104.00  -8.00   50
 18  ω     26.00  52.00   1.00    1.00    --  107.93 -94.00-120.00   26
 19  ω     55.00 109.00   1.00    1.00    --  107.93 -94.00-120.00   54
 20  ω     87.00 157.00   1.00    1.00    --  107.93  30.00 -30.00   70
 21  ω     25.00 158.00   1.00    1.00    --  107.93   0.00 -60.00  133
;

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

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 shelx_SHELXL_version_number            2018/3

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.2674P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.036
_refine_ls_R_factor_gt           0.034
_refine_ls_wR_factor_ref         0.0875
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   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
C C 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.05681(9) 0.37176(8) 0.01895(7) 0.02853(19) Uani 1 1 d . . . . .
F2 F 0.07001(10) 0.50167(10) 0.20160(8) 0.0373(2) Uani 1 1 d . . . . .
F3 F 0.16217(10) 0.32906(9) 0.18742(9) 0.0405(2) Uani 1 1 d . . . . .
O1 O 0.35338(11) 0.74261(10) -0.43765(8) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.44502(15) 0.80508(13) -0.31781(11) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.43114(14) 0.72782(13) -0.21993(11) 0.0190(2) Uani 1 1 d . . . . .
H2 H 0.354158 0.625236 -0.233558 0.023 Uiso 1 1 calc R . . . .
C3 C 0.53110(14) 0.80149(13) -0.10057(11) 0.0180(2) Uani 1 1 d . . . . .
C4 C 0.50654(14) 0.72685(13) 0.00942(11) 0.0180(2) Uani 1 1 d . . . . .
C5 C 0.35047(14) 0.61453(13) 0.01549(11) 0.0190(2) Uani 1 1 d . . . . .
H5 H 0.260594 0.581255 -0.053393 0.023 Uiso 1 1 calc R . . . .
C6 C 0.32626(14) 0.55137(12) 0.12184(11) 0.0191(2) Uani 1 1 d . . . . .
C7 C 0.45756(15) 0.59691(13) 0.22206(11) 0.0201(2) Uani 1 1 d . . . . .
H7 H 0.43992 0.551839 0.294038 0.024 Uiso 1 1 calc R . . . .
C8 C 0.61526(15) 0.70845(13) 0.21776(11) 0.0193(2) Uani 1 1 d . . . . .
C9 C 0.63953(14) 0.77706(12) 0.11232(11) 0.0182(2) Uani 1 1 d . . . . .
C10 C 0.80018(14) 0.90888(13) 0.10532(11) 0.0212(3) Uani 1 1 d . . . . .
H10A H 0.870561 0.873067 0.053149 0.025 Uiso 1 1 calc R . . . .
H10B H 0.865175 0.957087 0.191745 0.025 Uiso 1 1 calc R . . . .
C11 C 0.75848(15) 1.02345(13) 0.04658(11) 0.0219(3) Uani 1 1 d . . . . .
H11A H 0.698232 1.066884 0.103441 0.026 Uiso 1 1 calc R . . . .
H11B H 0.864324 1.106304 0.037457 0.026 Uiso 1 1 calc R . . . .
C12 C 0.65001(14) 0.95013(13) -0.08186(11) 0.0198(2) Uani 1 1 d . . . . .
C13 C 0.66035(15) 1.02594(14) -0.18133(12) 0.0234(3) Uani 1 1 d . . . . .
H13 H 0.739027 1.127838 -0.168772 0.028 Uiso 1 1 calc R . . . .
C14 C 0.55833(16) 0.95581(14) -0.29803(12) 0.0238(3) Uani 1 1 d . . . . .
H14 H 0.565348 1.00983 -0.364167 0.029 Uiso 1 1 calc R . . . .
C15 C 0.24362(19) 0.58670(15) -0.46238(13) 0.0319(3) Uani 1 1 d . . . . .
H15A H 0.187256 0.554519 -0.550861 0.048 Uiso 1 1 calc GR . . . .
H15B H 0.158804 0.570051 -0.40551 0.048 Uiso 1 1 calc GR . . . .
H15C H 0.309337 0.52833 -0.447769 0.048 Uiso 1 1 calc GR . . . .
C16 C 0.15605(15) 0.43885(13) 0.13217(11) 0.0222(3) Uani 1 1 d . . . . .
C17 C 0.75300(15) 0.75030(13) 0.32688(11) 0.0202(2) Uani 1 1 d . . . . .
C18 C 0.72458(16) 0.78514(14) 0.45107(11) 0.0231(3) Uani 1 1 d . . . . .
H18 H 0.618908 0.785831 0.465729 0.028 Uiso 1 1 calc R . . . .
C19 C 0.85012(17) 0.81889(14) 0.55360(12) 0.0267(3) Uani 1 1 d . . . . .
H19 H 0.829991 0.843004 0.637822 0.032 Uiso 1 1 calc R . . . .
C20 C 1.00389(17) 0.81742(14) 0.53321(12) 0.0270(3) Uani 1 1 d . . . . .
H20 H 1.089179 0.839808 0.603275 0.032 Uiso 1 1 calc R . . . .
C21 C 1.03330(16) 0.78312(14) 0.41002(12) 0.0256(3) Uani 1 1 d . . . . .
H21 H 1.139117 0.78242 0.395865 0.031 Uiso 1 1 calc R . . . .
C22 C 0.90889(15) 0.74984(14) 0.30748(12) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.93008 0.726575 0.223446 0.027 Uiso 1 1 calc R . . . .



#----------------------------------------------------------------------------#
#                   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
F1 C16 1.3431(14) . ?
F2 C16 1.3472(15) . ?
F3 C16 1.3358(14) . ?
O1 C1 1.3733(14) . ?
O1 C15 1.4253(16) . ?
C1 C2 1.3863(17) . ?
C1 C14 1.3966(17) . ?
C2 H2 0.95 . ?
C2 C3 1.4044(16) . ?
C3 C4 1.4827(16) . ?
C3 C12 1.3966(16) . ?
C4 C5 1.3937(16) . ?
C4 C9 1.4117(16) . ?
C5 H5 0.95 . ?
C5 C6 1.3850(16) . ?
C6 C7 1.3885(16) . ?
C6 C16 1.4916(16) . ?
C7 H7 0.95 . ?
C7 C8 1.3954(17) . ?
C8 C9 1.4052(17) . ?
C8 C17 1.4939(16) . ?
C9 C10 1.5111(16) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C10 C11 1.5277(17) . ?
C11 H11A 0.99 . ?
C11 H11B 0.99 . ?
C11 C12 1.5079(16) . ?
C12 C13 1.3943(17) . ?
C13 H13 0.95 . ?
C13 C14 1.3845(18) . ?
C14 H14 0.95 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C17 C18 1.3957(17) . ?
C17 C22 1.3938(17) . ?
C18 H18 0.95 . ?
C18 C19 1.3923(17) . ?
C19 H19 0.95 . ?
C19 C20 1.3816(19) . ?
C20 H20 0.95 . ?
C20 C21 1.3878(19) . ?
C21 H21 0.95 . ?
C21 C22 1.3872(17) . ?
C22 H22 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
C1 O1 C15 116.86(9) . . ?
O1 C1 C2 124.10(11) . . ?
O1 C1 C14 115.75(10) . . ?
C2 C1 C14 120.15(11) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.87(11) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 121.02(10) . . ?
C12 C3 C2 120.22(11) . . ?
C12 C3 C4 118.67(10) . . ?
C5 C4 C3 120.55(10) . . ?
C5 C4 C9 119.89(11) . . ?
C9 C4 C3 119.43(10) . . ?
C4 C5 H5 120 . . ?
C6 C5 C4 120.07(11) . . ?
C6 C5 H5 120 . . ?
C5 C6 C7 120.52(11) . . ?
C5 C6 C16 120.03(10) . . ?
C7 C6 C16 119.39(10) . . ?
C6 C7 H7 119.8 . . ?
C6 C7 C8 120.44(11) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 119.52(11) . . ?
C7 C8 C17 118.10(10) . . ?
C9 C8 C17 122.38(10) . . ?
C4 C9 C10 117.34(10) . . ?
C8 C9 C4 119.49(11) . . ?
C8 C9 C10 123.11(10) . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C9 C10 C11 110.05(9) . . ?
H10A C10 H10B 108.2 . . ?
C11 C10 H10A 109.7 . . ?
C11 C10 H10B 109.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.63(10) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C3 C12 C11 118.52(10) . . ?
C13 C12 C3 118.75(11) . . ?
C13 C12 C11 122.70(11) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.37(11) . . ?
C14 C13 H13 119.3 . . ?
C1 C14 H14 120.2 . . ?
C13 C14 C1 119.51(11) . . ?
C13 C14 H14 120.2 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
F1 C16 F2 105.42(10) . . ?
F1 C16 C6 112.91(10) . . ?
F2 C16 C6 112.23(10) . . ?
F3 C16 F1 106.66(10) . . ?
F3 C16 F2 105.96(10) . . ?
F3 C16 C6 113.08(10) . . ?
C18 C17 C8 120.00(11) . . ?
C22 C17 C8 121.09(11) . . ?
C22 C17 C18 118.87(11) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.41(12) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.20(12) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.76(11) . . ?
C21 C20 H20 120.1 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.30(12) . . ?
C22 C21 H21 119.8 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.45(11) . . ?
C21 C22 H22 119.8 . . ?

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 179.71(10) . . . . ?
O1 C1 C14 C13 -177.58(10) . . . . ?
C1 C2 C3 C4 173.60(10) . . . . ?
C1 C2 C3 C12 -3.00(17) . . . . ?
C2 C1 C14 C13 2.06(18) . . . . ?
C2 C3 C4 C5 -26.00(16) . . . . ?
C2 C3 C4 C9 158.08(11) . . . . ?
C2 C3 C12 C11 -178.12(10) . . . . ?
C2 C3 C12 C13 3.66(17) . . . . ?
C3 C4 C5 C6 -176.44(10) . . . . ?
C3 C4 C9 C8 178.71(10) . . . . ?
C3 C4 C9 C10 1.55(15) . . . . ?
C3 C12 C13 C14 -1.49(18) . . . . ?
C4 C3 C12 C11 5.19(16) . . . . ?
C4 C3 C12 C13 -173.02(10) . . . . ?
C4 C5 C6 C7 -1.28(17) . . . . ?
C4 C5 C6 C16 175.77(10) . . . . ?
C4 C9 C10 C11 38.41(14) . . . . ?
C5 C4 C9 C8 2.76(16) . . . . ?
C5 C4 C9 C10 -174.40(10) . . . . ?
C5 C6 C7 C8 0.84(17) . . . . ?
C5 C6 C16 F1 21.77(16) . . . . ?
C5 C6 C16 F2 -97.20(13) . . . . ?
C5 C6 C16 F3 142.99(11) . . . . ?
C6 C7 C8 C9 1.40(17) . . . . ?
C6 C7 C8 C17 -178.53(10) . . . . ?
C7 C6 C16 F1 -161.15(10) . . . . ?
C7 C6 C16 F2 79.88(14) . . . . ?
C7 C6 C16 F3 -39.93(15) . . . . ?
C7 C8 C9 C4 -3.18(16) . . . . ?
C7 C8 C9 C10 173.81(10) . . . . ?
C7 C8 C17 C18 -50.64(15) . . . . ?
C7 C8 C17 C22 126.91(12) . . . . ?
C8 C9 C10 C11 -138.64(11) . . . . ?
C8 C17 C18 C19 177.64(11) . . . . ?
C8 C17 C22 C21 -177.42(11) . . . . ?
C9 C4 C5 C6 -0.54(17) . . . . ?
C9 C8 C17 C18 129.42(12) . . . . ?
C9 C8 C17 C22 -53.03(16) . . . . ?
C9 C10 C11 C12 -55.72(13) . . . . ?
C10 C11 C12 C3 35.06(14) . . . . ?
C10 C11 C12 C13 -146.80(11) . . . . ?
C11 C12 C13 C14 -179.62(11) . . . . ?
C12 C3 C4 C5 150.66(11) . . . . ?
C12 C3 C4 C9 -25.26(15) . . . . ?
C12 C13 C14 C1 -1.37(18) . . . . ?
C14 C1 C2 C3 0.11(17) . . . . ?
C15 O1 C1 C2 -2.97(17) . . . . ?
C15 O1 C1 C14 176.65(11) . . . . ?
C16 C6 C7 C8 -176.22(11) . . . . ?
C17 C8 C9 C4 176.76(10) . . . . ?
C17 C8 C9 C10 -6.26(17) . . . . ?
C17 C18 C19 C20 -0.33(19) . . . . ?
C18 C17 C22 C21 0.16(18) . . . . ?
C18 C19 C20 C21 0.42(19) . . . . ?
C19 C20 C21 C22 -0.23(19) . . . . ?
C20 C21 C22 C17 -0.06(19) . . . . ?
C22 C17 C18 C19 0.04(18) . . . . ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
