# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1947537'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F2 O'
_chemical_formula_moiety         'C16 H12 F2 O'
_chemical_formula_weight         258.27
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        Iba2
_space_group_name_Hall           'I 2 -2c'
_space_group_IT_number           45
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
#------------------------------------------------------------------------------
_cell_length_a                   14.2552(3)
_cell_length_b                   22.1202(7)
_cell_length_c                   7.4973(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2364.11(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3566
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      74.30
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072.00
_exptl_absorpt_coefficient_mu    0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.691
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device       'AFC11: Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13323
_diffrn_reflns_av_unetI/netI     0.0833
_diffrn_reflns_av_R_equivalents  0.1145
_diffrn_reflns_theta_max         75.500
_diffrn_reflns_theta_min         3.689
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2383
_reflns_number_gt                1947
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_max     0.944
_reflns_Friedel_fraction_full    0.974

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1248
_refine_ls_number_restraints     27
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2383
_refine_ls_number_parameters     185
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0630P)²+0.9895P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(18)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F15 F 0.65185(19) 0.36836(13) 0.1584(4) 0.0401(8) Uani 0.839(6) 1 d . U P A 1
F16 F 0.61064(18) 0.48867(11) 0.5782(4) 0.0352(7) Uani 0.839(6) 1 d . U P A 1
O1 O 0.5885(2) 0.40900(15) 0.3920(5) 0.0316(8) Uani 0.839(6) 1 d . U P A 1
F15A F 0.740(2) 0.4212(15) 0.214(4) 0.112(10) Uiso 0.161(6) 1 d D U P A 2
F16A F 0.4971(16) 0.4188(11) 0.550(4) 0.094(8) Uiso 0.161(6) 1 d D U P A 2
O1A O 0.644(3) 0.4450(18) 0.420(6) 0.108(11) Uiso 0.161(6) 1 d . U P A 2
C1 C 0.7372(3) 0.34995(19) 0.4258(6) 0.0368(9) Uani 1 1 d . . . . .
H1 H 0.781963 0.328882 0.344057 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7917(3) 0.38513(17) 0.5656(7) 0.0358(9) Uani 1 1 d . . . . .
C3 C 0.8877(3) 0.39558(18) 0.5589(7) 0.0385(10) Uani 1 1 d . . . . .
H3 H 0.923931 0.379640 0.463479 0.046 Uiso 1 1 calc R U . . .
C4 C 0.9306(3) 0.42916(18) 0.6913(7) 0.0407(10) Uani 1 1 d . . . . .
H4 H 0.996292 0.436240 0.686424 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8783(3) 0.45261(18) 0.8311(7) 0.0407(10) Uani 1 1 d . . . . .
H5 H 0.907728 0.476387 0.920537 0.049 Uiso 1 1 calc R U . . .
C6 C 0.7828(3) 0.44109(18) 0.8394(6) 0.0384(10) Uani 1 1 d . . . . .
H6 H 0.746951 0.456596 0.935936 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7392(3) 0.40720(17) 0.7081(6) 0.0332(9) Uani 1 1 d . . . . .
C8 C 0.6353(3) 0.39149(18) 0.7073(6) 0.0363(10) Uani 1 1 d . . . . .
H8 H 0.608464 0.399377 0.828326 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6228(3) 0.32483(17) 0.6612(6) 0.0328(9) Uani 1 1 d . . . . .
C10 C 0.5619(3) 0.28663(19) 0.7475(6) 0.0381(10) Uani 1 1 d . . . . .
H10 H 0.525092 0.301061 0.844173 0.046 Uiso 1 1 calc R U . . .
C11 C 0.5543(3) 0.22666(18) 0.6927(7) 0.0401(10) Uani 1 1 d . . . . .
H11 H 0.511877 0.200211 0.751578 0.048 Uiso 1 1 calc R U . . .
C12 C 0.6084(3) 0.20556(18) 0.5527(7) 0.0404(10) Uani 1 1 d . . . . .
H12 H 0.603741 0.164456 0.517041 0.048 Uiso 1 1 calc R U . . .
C13 C 0.6694(3) 0.24400(19) 0.4643(6) 0.0377(10) Uani 1 1 d . . . . .
H13 H 0.706509 0.229426 0.368272 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6758(3) 0.30403(19) 0.5172(6) 0.0339(9) Uani 1 1 d . . . . .
C15 C 0.6769(3) 0.3946(2) 0.3184(6) 0.0387(10) Uani 1 1 d D . . . .
H15A H 0.713148 0.432532 0.295735 0.046 Uiso 0.839(6) 1 calc R U P A 1
H15B H 0.625862 0.374199 0.249444 0.046 Uiso 0.161(6) 1 calc R U P A 2
C16 C 0.5820(3) 0.42912(18) 0.5690(7) 0.0382(9) Uani 1 1 d D . . . .
H16A H 0.514187 0.428054 0.602706 0.046 Uiso 0.839(6) 1 calc R U P A 1
H16B H 0.579104 0.468849 0.632373 0.046 Uiso 0.161(6) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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
F15 C15 1.380(6) . ?
F16 C16 1.381(5) . ?
O1 C16 1.402(6) . ?
O1 C15 1.412(6) . ?
F15A C15 1.33(2) . ?
F16A C16 1.24(2) . ?
O1A C15 1.43(4) . ?
O1A C16 1.46(4) . ?
C1 C14 1.506(6) . ?
C1 C2 1.519(6) . ?
C1 C15 1.537(6) . ?
C1 H1 1.0000 . ?
C2 C3 1.390(6) . ?
C2 C7 1.393(6) . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.520(6) . ?
C8 C9 1.525(5) . ?
C8 C16 1.532(6) . ?
C8 H8 1.0000 . ?
C9 C10 1.373(6) . ?
C9 C14 1.396(6) . ?
C10 C11 1.393(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(6) . ?
C13 H13 0.9500 . ?
C15 H15A 1.0000 . ?
C15 H15B 1.0000 . ?
C16 H16A 1.0000 . ?
C16 H16B 1.0000 . ?

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
C16 O1 C15 120.0(3) . . ?
C15 O1A C16 115(3) . . ?
C14 C1 C2 109.2(4) . . ?
C14 C1 C15 110.3(3) . . ?
C2 C1 C15 108.5(3) . . ?
C14 C1 H1 109.6 . . ?
C2 C1 H1 109.6 . . ?
C15 C1 H1 109.6 . . ?
C3 C2 C7 119.9(4) . . ?
C3 C2 C1 124.4(4) . . ?
C7 C2 C1 115.7(4) . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 119.6(4) . . ?
C6 C7 C8 124.3(4) . . ?
C2 C7 C8 116.1(4) . . ?
C7 C8 C9 109.6(3) . . ?
C7 C8 C16 111.2(3) . . ?
C9 C8 C16 108.3(4) . . ?
C7 C8 H8 109.2 . . ?
C9 C8 H8 109.2 . . ?
C16 C8 H8 109.2 . . ?
C10 C9 C14 120.2(4) . . ?
C10 C9 C8 124.2(4) . . ?
C14 C9 C8 115.5(4) . . ?
C9 C10 C11 119.8(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.1(4) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 119.5(4) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C9 120.0(4) . . ?
C13 C14 C1 123.6(4) . . ?
C9 C14 C1 116.4(4) . . ?
F15 C15 O1 101.8(3) . . ?
F15A C15 O1A 101(2) . . ?
F15A C15 C1 102.4(15) . . ?
F15 C15 C1 109.2(4) . . ?
O1 C15 C1 116.1(4) . . ?
O1A C15 C1 113.9(17) . . ?
F15 C15 H15A 109.8 . . ?
O1 C15 H15A 109.8 . . ?
C1 C15 H15A 109.8 . . ?
F15A C15 H15B 112.8 . . ?
O1A C15 H15B 112.8 . . ?
C1 C15 H15B 112.8 . . ?
F16 C16 O1 109.3(4) . . ?
F16A C16 O1A 123(2) . . ?
F16A C16 C8 117.5(14) . . ?
F16 C16 C8 109.7(4) . . ?
O1 C16 C8 115.8(3) . . ?
O1A C16 C8 110.4(16) . . ?
F16 C16 H16A 107.2 . . ?
O1 C16 H16A 107.2 . . ?
C8 C16 H16A 107.2 . . ?
F16A C16 H16B 100.1 . . ?
O1A C16 H16B 100.1 . . ?
C8 C16 H16B 100.1 . . ?

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
C14 C1 C2 C3 131.4(4) . . . . ?
C15 C1 C2 C3 -108.3(5) . . . . ?
C14 C1 C2 C7 -48.1(5) . . . . ?
C15 C1 C2 C7 72.1(5) . . . . ?
C7 C2 C3 C4 -1.7(6) . . . . ?
C1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C6 1.3(6) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C5 C6 C7 C2 -0.8(6) . . . . ?
C5 C6 C7 C8 179.1(4) . . . . ?
C3 C2 C7 C6 2.1(6) . . . . ?
C1 C2 C7 C6 -178.4(4) . . . . ?
C3 C2 C7 C8 -177.8(4) . . . . ?
C1 C2 C7 C8 1.8(5) . . . . ?
C6 C7 C8 C9 -134.8(4) . . . . ?
C2 C7 C8 C9 45.0(5) . . . . ?
C6 C7 C8 C16 105.5(5) . . . . ?
C2 C7 C8 C16 -74.7(4) . . . . ?
C7 C8 C9 C10 136.5(4) . . . . ?
C16 C8 C9 C10 -102.0(5) . . . . ?
C7 C8 C9 C14 -45.7(5) . . . . ?
C16 C8 C9 C14 75.7(4) . . . . ?
C14 C9 C10 C11 1.1(6) . . . . ?
C8 C9 C10 C11 178.7(4) . . . . ?
C9 C10 C11 C12 0.5(6) . . . . ?
C10 C11 C12 C13 -1.0(7) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C9 1.6(6) . . . . ?
C12 C13 C14 C1 -177.7(4) . . . . ?
C10 C9 C14 C13 -2.1(6) . . . . ?
C8 C9 C14 C13 -180.0(4) . . . . ?
C10 C9 C14 C1 177.2(4) . . . . ?
C8 C9 C14 C1 -0.6(5) . . . . ?
C2 C1 C14 C13 -133.2(4) . . . . ?
C15 C1 C14 C13 107.6(5) . . . . ?
C2 C1 C14 C9 47.5(5) . . . . ?
C15 C1 C14 C9 -71.7(5) . . . . ?
C16 O1 C15 F15 170.9(3) . . . . ?
C16 O1 C15 C1 52.4(5) . . . . ?
C16 O1A C15 F15A -171(3) . . . . ?
C16 O1A C15 C1 -62(3) . . . . ?
C14 C1 C15 F15A -165.1(16) . . . . ?
C2 C1 C15 F15A 75.3(16) . . . . ?
C14 C1 C15 F15 -80.1(4) . . . . ?
C2 C1 C15 F15 160.3(3) . . . . ?
C14 C1 C15 O1 34.2(5) . . . . ?
C2 C1 C15 O1 -85.4(4) . . . . ?
C14 C1 C15 O1A 86.7(19) . . . . ?
C2 C1 C15 O1A -32.9(19) . . . . ?
C15 O1 C16 F16 76.2(4) . . . . ?
C15 O1 C16 C8 -48.3(5) . . . . ?
C15 O1A C16 F16A -82(3) . . . . ?
C15 O1A C16 C8 64(3) . . . . ?
C7 C8 C16 F16A 177.1(15) . . . . ?
C9 C8 C16 F16A 56.6(16) . . . . ?
C7 C8 C16 F16 -44.3(5) . . . . ?
C9 C8 C16 F16 -164.8(3) . . . . ?
C7 C8 C16 O1 80.0(4) . . . . ?
C9 C8 C16 O1 -40.4(5) . . . . ?
C7 C8 C16 O1A 29.2(18) . . . . ?
C9 C8 C16 O1A -91.3(18) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform'
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1947539'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F2'
_chemical_formula_moiety         'C16 H12 F2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        R-3
_space_group_name_Hall           '-R 3'
_space_group_IT_number           148
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
#------------------------------------------------------------------------------
_cell_length_a                   34.4377(4)
_cell_length_b                   34.4377(4)
_cell_length_c                   5.42477(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     5571.60(12)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    10916
_cell_measurement_theta_min      4.43
_cell_measurement_theta_max      74.63
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2268.00
_exptl_absorpt_coefficient_mu    0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_T_max  0.992

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device       'AFC11: Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22504
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_theta_max         75.485
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2550
_reflns_number_gt                2228
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1198
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2550
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0668P)²+4.1774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.19587(3) 0.32724(3) 0.05982(16) 0.0461(2) Uani 1 1 d . . . . .
F2 F 0.12158(3) 0.28752(3) 0.06603(17) 0.0502(3) Uani 1 1 d . . . . .
C1 C 0.16151(5) 0.26210(5) 0.3090(2) 0.0354(3) Uani 1 1 d . . . . .
H1 H 0.160049 0.280953 0.444864 0.042 Uiso 1 1 calc R U . . .
C2 C 0.20532(5) 0.26205(5) 0.3413(2) 0.0339(3) Uani 1 1 d . . . . .
C3 C 0.23435(5) 0.28818(5) 0.5289(2) 0.0372(3) Uani 1 1 d . . . . .
H3 H 0.226170 0.305197 0.632341 0.045 Uiso 1 1 calc R U . . .
C4 C 0.27494(5) 0.28979(5) 0.5673(3) 0.0407(3) Uani 1 1 d . . . . .
H4 H 0.293956 0.307149 0.698638 0.049 Uiso 1 1 calc R U . . .
C5 C 0.28762(5) 0.26607(5) 0.4140(3) 0.0435(4) Uani 1 1 d . . . . .
H5 H 0.315417 0.267112 0.439491 0.052 Uiso 1 1 calc R U . . .
C6 C 0.25977(5) 0.24077(5) 0.2232(3) 0.0416(3) Uani 1 1 d . . . . .
H6 H 0.269222 0.225426 0.114896 0.050 Uiso 1 1 calc R U . . .
C7 C 0.21773(5) 0.23735(5) 0.1865(3) 0.0360(3) Uani 1 1 d . . . . .
C8 C 0.18910(5) 0.20748(5) -0.0093(3) 0.0399(3) Uani 1 1 d . . . . .
H8 H 0.204104 0.204821 -0.149720 0.048 Uiso 1 1 calc R U . . .
C9 C 0.14427(5) 0.18348(5) -0.0136(3) 0.0414(3) Uani 1 1 d . . . . .
H9 H 0.131268 0.166186 -0.158077 0.050 Uiso 1 1 calc R U . . .
C10 C 0.11278(5) 0.18058(5) 0.1769(3) 0.0391(3) Uani 1 1 d . . . . .
C11 C 0.07285(5) 0.13950(6) 0.2050(3) 0.0489(4) Uani 1 1 d . . . . .
H11 H 0.066663 0.115505 0.095889 0.059 Uiso 1 1 calc R U . . .
C12 C 0.04230(5) 0.13323(6) 0.3884(4) 0.0542(4) Uani 1 1 d . . . . .
H12 H 0.015860 0.104909 0.407223 0.065 Uiso 1 1 calc R U . . .
C13 C 0.05032(5) 0.16825(7) 0.5441(3) 0.0536(4) Uani 1 1 d . . . . .
H13 H 0.029412 0.164070 0.670134 0.064 Uiso 1 1 calc R U . . .
C14 C 0.08886(5) 0.20936(6) 0.5159(3) 0.0453(4) Uani 1 1 d . . . . .
H14 H 0.093929 0.233491 0.621203 0.054 Uiso 1 1 calc R U . . .
C15 C 0.12049(5) 0.21602(5) 0.3351(3) 0.0370(3) Uani 1 1 d . . . . .
C16 C 0.16022(5) 0.28389(5) 0.0692(3) 0.0390(3) Uani 1 1 d . . . . .
H16 H 0.160744 0.266095 -0.075166 0.047 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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 1.3804(17) . ?
F2 C16 1.3974(16) . ?
C1 C16 1.514(2) . ?
C1 C15 1.514(2) . ?
C1 C2 1.5197(18) . ?
C1 H1 1.0000 . ?
C2 C3 1.395(2) . ?
C2 C7 1.4052(19) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.464(2) . ?
C8 C9 1.338(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.465(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C10 C15 1.405(2) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(2) . ?
C14 H14 0.9500 . ?
C16 H16 1.0000 . ?

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
C16 C1 C15 110.89(11) . . ?
C16 C1 C2 112.02(11) . . ?
C15 C1 C2 113.25(11) . . ?
C16 C1 H1 106.7 . . ?
C15 C1 H1 106.7 . . ?
C2 C1 H1 106.7 . . ?
C3 C2 C7 119.33(13) . . ?
C3 C2 C1 118.37(12) . . ?
C7 C2 C1 122.29(12) . . ?
C4 C3 C2 121.21(13) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.79(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 119.89(14) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C7 121.26(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 118.44(13) . . ?
C2 C7 C8 123.86(13) . . ?
C6 C7 C8 117.68(13) . . ?
C9 C8 C7 127.58(14) . . ?
C9 C8 H8 116.2 . . ?
C7 C8 H8 116.2 . . ?
C8 C9 C10 128.02(14) . . ?
C8 C9 H9 116.0 . . ?
C10 C9 H9 116.0 . . ?
C11 C10 C15 118.29(14) . . ?
C11 C10 C9 117.65(14) . . ?
C15 C10 C9 124.05(14) . . ?
C12 C11 C10 121.36(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C13 C12 C11 119.89(16) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 119.76(15) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.12(16) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 119.55(14) . . ?
C14 C15 C1 118.70(13) . . ?
C10 C15 C1 121.71(12) . . ?
F1 C16 F2 105.94(11) . . ?
F1 C16 C1 109.69(11) . . ?
F2 C16 C1 108.67(11) . . ?
F1 C16 H16 110.8 . . ?
F2 C16 H16 110.8 . . ?
C1 C16 H16 110.8 . . ?

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
C16 C1 C2 C3 112.97(14) . . . . ?
C15 C1 C2 C3 -120.70(14) . . . . ?
C16 C1 C2 C7 -65.84(17) . . . . ?
C15 C1 C2 C7 60.49(17) . . . . ?
C7 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C4 -179.66(13) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C4 C5 C6 C7 -2.3(2) . . . . ?
C3 C2 C7 C6 -1.5(2) . . . . ?
C1 C2 C7 C6 177.32(12) . . . . ?
C3 C2 C7 C8 177.43(13) . . . . ?
C1 C2 C7 C8 -3.8(2) . . . . ?
C5 C6 C7 C2 3.0(2) . . . . ?
C5 C6 C7 C8 -175.94(13) . . . . ?
C2 C7 C8 C9 -31.4(2) . . . . ?
C6 C7 C8 C9 147.51(16) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
C8 C9 C10 C11 -146.36(16) . . . . ?
C8 C9 C10 C15 32.5(2) . . . . ?
C15 C10 C11 C12 -2.1(2) . . . . ?
C9 C10 C11 C12 176.80(14) . . . . ?
C10 C11 C12 C13 1.8(2) . . . . ?
C11 C12 C13 C14 0.0(2) . . . . ?
C12 C13 C14 C15 -1.3(2) . . . . ?
C13 C14 C15 C10 0.9(2) . . . . ?
C13 C14 C15 C1 178.56(14) . . . . ?
C11 C10 C15 C14 0.8(2) . . . . ?
C9 C10 C15 C14 -178.04(13) . . . . ?
C11 C10 C15 C1 -176.83(13) . . . . ?
C9 C10 C15 C1 4.4(2) . . . . ?
C16 C1 C15 C14 -111.47(14) . . . . ?
C2 C1 C15 C14 121.60(14) . . . . ?
C16 C1 C15 C10 66.15(16) . . . . ?
C2 C1 C15 C10 -60.78(17) . . . . ?
C15 C1 C16 F1 174.79(11) . . . . ?
C2 C1 C16 F1 -57.61(15) . . . . ?
C15 C1 C16 F2 59.40(15) . . . . ?
C2 C1 C16 F2 -173.00(11) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pentane'
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1947538'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H12 F2 O'
_chemical_formula_sum            'C16 H12 F2 O'
_chemical_formula_weight         258.26
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        P31
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   8.8519(6)
_cell_length_b                   8.8519(6)
_cell_length_c                   13.9613(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     947.39(15)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    3941
_cell_measurement_temperature    178
_cell_measurement_theta_max      67.3480
_cell_measurement_theta_min      3.1470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             402
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9709
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.691
_diffrn_reflns_theta_min         5.772
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ      0.00 200.00   0.50   20.00   0.00 -30.00   0.00    --   400
  2  ω    -72.00   1.00   0.50   20.00    --  -30.00 -72.00 -90.00  146
  3  ω   -113.00 -71.00   0.50   20.00    --  -30.00 180.00 -45.00   84
  4  φ      0.00 200.00   0.50   20.00   0.00 -67.00   0.00    --   400
  5  ω    -85.00 -13.00   0.50   20.00    --  -67.00  72.00  90.00  144
  6  ω   -133.00 -93.00   0.50   20.00    --  -67.00 180.00   0.00   80
  7  ω    -85.00 -12.00   0.50   20.00    --  -67.00  72.00 -90.00  146
  8  ω   -126.00 -86.00   0.50   20.00    --  -67.00 180.00-180.00   80
  9  φ      0.00 200.00   0.50   20.00 -25.00-110.00   0.00    --   400
 10  ω   -128.00 -20.00   0.50   20.00    -- -110.00  72.00-135.00  216
 11  ω   -128.00 -20.00   0.50   20.00    -- -110.00  72.00  45.00  216
 12  ω   -115.00 -20.00   0.50   20.00    -- -110.00  72.00 -45.00  190
 13  ω   -113.00 -23.00   0.50   20.00    -- -110.00  72.00 135.00  180
 14  ω   -141.00 -46.00   0.50   20.00    -- -110.00 180.00 -90.00  190
 15  ω   -141.00 -46.00   0.50   20.00    -- -110.00 180.00-180.00  190
 16  ω   -141.00 -59.00   0.50   20.00    -- -110.00 180.00  90.00  164
 17  ω   -141.00 -55.00   0.50   20.00    -- -110.00 180.00   0.00  172
 18  ω   -141.00 -59.00   0.50   20.00    -- -110.00 180.00  45.00  164
 19  ω   -141.00 -78.00   0.50   20.00    -- -110.00 180.00 -45.00  126
 20  ω   -140.00 -77.00   0.50   20.00    -- -110.00 180.00-135.00  126
 21  ω   -140.00 -56.00   0.50   20.00    -- -110.00 180.00 135.00  168
 22  ω    -91.00 -90.50   0.50   20.00    --  -30.00  45.00   0.00    1
;
_diffrn_measurement_device       'AFC12: Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1163323000
_diffrn_orient_matrix_UB_12      0.0518287000
_diffrn_orient_matrix_UB_13      0.0895580000
_diffrn_orient_matrix_UB_21      0.1596371000
_diffrn_orient_matrix_UB_22      0.0451671000
_diffrn_orient_matrix_UB_23      -0.0637290000
_diffrn_orient_matrix_UB_31      0.0355031000
_diffrn_orient_matrix_UB_32      0.1884639000
_diffrn_orient_matrix_UB_33      -0.0094487000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                1882
_reflns_number_total             2225
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_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         0.438
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2225
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0695
_refine_ls_restrained_S_all      1.058
_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)+(0.1611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2035
_refine_ls_wR_factor_ref         0.2084
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8), C15(H15), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
;
_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
F15 F 0.9666(5) 0.9796(5) 0.4483(3) 0.1055(11) Uani 1 1 d . . . . .
F16 F 0.7823(6) 0.6643(7) 0.3111(3) 0.1154(13) Uani 1 1 d . . . . .
O1 O 1.0153(6) 0.7577(6) 0.4090(3) 0.0948(11) Uani 1 1 d . . . . .
C1 C 0.8951(7) 0.7648(7) 0.5693(3) 0.0760(11) Uani 1 1 d . . . . .
H1 H 0.932145 0.845171 0.625629 0.091 Uiso 1 1 calc R . . . .
C2 C 0.7054(7) 0.7028(8) 0.5474(3) 0.0789(12) Uani 1 1 d . . . . .
C3 C 0.6140(9) 0.7775(11) 0.5848(5) 0.0971(17) Uani 1 1 d . . . . .
H3 H 0.671990 0.875443 0.626093 0.117 Uiso 1 1 calc R . . . .
C4 C 0.4429(11) 0.7140(16) 0.5639(5) 0.122(3) Uani 1 1 d . . . . .
H4 H 0.380972 0.766488 0.589956 0.146 Uiso 1 1 calc R . . . .
C5 C 0.3602(10) 0.5698(16) 0.5032(6) 0.122(3) Uani 1 1 d . . . . .
H5 H 0.240644 0.524196 0.487599 0.146 Uiso 1 1 calc R . . . .
C6 C 0.4502(9) 0.4913(11) 0.4649(5) 0.103(2) Uani 1 1 d . . . . .
H6 H 0.391805 0.391344 0.425019 0.124 Uiso 1 1 calc R . . . .
C7 C 0.6256(7) 0.5614(8) 0.4860(3) 0.0832(13) Uani 1 1 d . . . . .
C8 C 0.7363(8) 0.4876(8) 0.4485(4) 0.0855(13) Uani 1 1 d . . . . .
H8 H 0.659335 0.371483 0.418182 0.103 Uiso 1 1 calc R . . . .
C9 C 0.8331(7) 0.4659(8) 0.5319(4) 0.0813(12) Uani 1 1 d . . . . .
C10 C 0.8477(9) 0.3191(8) 0.5485(5) 0.0942(15) Uani 1 1 d . . . . .
H10 H 0.794922 0.222641 0.505856 0.113 Uiso 1 1 calc R . . . .
C11 C 0.9409(9) 0.3139(9) 0.6286(5) 0.0993(17) Uani 1 1 d . . . . .
H11 H 0.948687 0.212581 0.641493 0.119 Uiso 1 1 calc R . . . .
C12 C 1.0201(8) 0.4547(9) 0.6875(5) 0.0931(16) Uani 1 1 d . . . . .
H12 H 1.084735 0.451261 0.740978 0.112 Uiso 1 1 calc R . . . .
C13 C 1.0085(7) 0.6023(8) 0.6715(4) 0.0803(12) Uani 1 1 d . . . . .
H13 H 1.064236 0.698883 0.713861 0.096 Uiso 1 1 calc R . . . .
C14 C 0.9155(6) 0.6094(7) 0.5934(3) 0.0740(11) Uani 1 1 d . . . . .
C15 C 1.0131(8) 0.8611(8) 0.4839(4) 0.0848(13) Uani 1 1 d . . . . .
H15 H 1.135088 0.930285 0.508827 0.102 Uiso 1 1 calc R . . . .
C16 C 0.8689(9) 0.6125(10) 0.3740(4) 0.0950(16) Uani 1 1 d . . . . .
H16 H 0.909866 0.543731 0.336232 0.114 Uiso 1 1 calc 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
F15 C15 1.396(7) . ?
F16 C16 1.385(8) . ?
O1 C15 1.397(8) . ?
O1 C16 1.380(8) . ?
C1 H1 1.0000 . ?
C1 C2 1.514(8) . ?
C1 C14 1.512(8) . ?
C1 C15 1.532(7) . ?
C2 C3 1.378(9) . ?
C2 C7 1.384(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.396(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.399(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(9) . ?
C7 C8 1.517(9) . ?
C8 H8 1.0000 . ?
C8 C9 1.514(7) . ?
C8 C16 1.545(9) . ?
C9 C10 1.388(9) . ?
C9 C14 1.399(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.404(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.360(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(7) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?

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
C16 O1 C15 124.2(5) . . ?
C2 C1 H1 109.0 . . ?
C2 C1 C15 111.6(4) . . ?
C14 C1 H1 109.0 . . ?
C14 C1 C2 109.3(4) . . ?
C14 C1 C15 108.8(4) . . ?
C15 C1 H1 109.0 . . ?
C3 C2 C1 124.1(6) . . ?
C3 C2 C7 120.8(6) . . ?
C7 C2 C1 115.1(5) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(8) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.4(8) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(7) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.1(8) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 C6 119.1(6) . . ?
C2 C7 C8 117.1(5) . . ?
C6 C7 C8 123.7(6) . . ?
C7 C8 H8 109.5 . . ?
C7 C8 C16 110.3(5) . . ?
C9 C8 C7 108.6(4) . . ?
C9 C8 H8 109.5 . . ?
C9 C8 C16 109.5(5) . . ?
C16 C8 H8 109.5 . . ?
C10 C9 C8 124.8(5) . . ?
C10 C9 C14 119.9(5) . . ?
C14 C9 C8 115.3(5) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(6) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(6) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.5(6) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(5) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C1 116.4(4) . . ?
C13 C14 C1 124.1(5) . . ?
C13 C14 C9 119.5(5) . . ?
F15 C15 O1 109.3(5) . . ?
F15 C15 C1 108.7(4) . . ?
F15 C15 H15 107.3 . . ?
O1 C15 C1 116.5(4) . . ?
O1 C15 H15 107.3 . . ?
C1 C15 H15 107.3 . . ?
F16 C16 C8 108.4(5) . . ?
F16 C16 H16 107.2 . . ?
O1 C16 F16 109.5(6) . . ?
O1 C16 C8 116.8(5) . . ?
O1 C16 H16 107.2 . . ?
C8 C16 H16 107.2 . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/petroleum ether'
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1947540'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2018-03-11
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F2'
_chemical_formula_moiety         'C16 H12 F2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   10.4484(5)
_cell_length_b                   12.8848(4)
_cell_length_c                   8.6234(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 100.333(4)
_cell_angle_gamma                90.0000
_cell_volume                     1142.10(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3261
_cell_measurement_theta_min      4.30
_cell_measurement_theta_max      74.33
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504.00
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.575
_exptl_absorpt_correction_T_max  0.991

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device       'AFC11: Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            12689
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_theta_max         75.916
_diffrn_reflns_theta_min         4.301
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2325
_reflns_number_gt                1734
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1781
_refine_ls_wR_factor_gt          0.1645
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2325
_refine_ls_number_parameters     164
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1057P)²+0.1349P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.28
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0055(16)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.71341(13) 0.53048(10) 0.82461(17) 0.0497(4) Uani 1 1 d . . . . .
F2 F 0.85394(14) 0.51857(10) 0.58051(18) 0.0535(5) Uani 1 1 d . . . . .
C1 C 0.6623(2) 0.48771(15) 0.6759(3) 0.0420(6) Uani 1 1 d . . . . .
H1 H 0.6296 0.5465 0.6038 0.050 Uiso 1 1 calc R U . . .
C2 C 0.7726(2) 0.43783(16) 0.6137(3) 0.0403(6) Uani 1 1 d . . . . .
H2 H 0.7373 0.4000 0.5139 0.048 Uiso 1 1 calc R U . . .
C3 C 0.8522(2) 0.36415(15) 0.7272(3) 0.0352(5) Uani 1 1 d . . . . .
C4 C 0.9549(2) 0.40011(16) 0.8396(3) 0.0397(5) Uani 1 1 d . . . . .
H4 H 0.9728 0.4724 0.8470 0.048 Uiso 1 1 calc R U . . .
C5 C 1.0309(2) 0.33258(18) 0.9403(3) 0.0426(6) Uani 1 1 d . . . . .
H5 H 1.0995 0.3583 1.0184 0.051 Uiso 1 1 calc R U . . .
C6 C 1.0068(2) 0.22623(17) 0.9270(3) 0.0413(5) Uani 1 1 d . . . . .
H6 H 1.0594 0.1790 0.9952 0.050 Uiso 1 1 calc R U . . .
C7 C 0.9064(2) 0.19015(16) 0.8146(3) 0.0377(5) Uani 1 1 d . . . . .
H7 H 0.8918 0.1175 0.8046 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8252(2) 0.25790(16) 0.7147(3) 0.0350(5) Uani 1 1 d . . . . .
C9 C 0.7210(2) 0.21675(15) 0.5935(3) 0.0380(5) Uani 1 1 d . . . . .
H9 H 0.7446 0.1601 0.5339 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5976(2) 0.24795(15) 0.5555(3) 0.0372(5) Uani 1 1 d . . . . .
H10 H 0.5520 0.2193 0.4598 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5180(2) 0.31961(15) 0.6357(2) 0.0358(5) Uani 1 1 d . . . . .
C12 C 0.3982(2) 0.27665(16) 0.6527(3) 0.0396(5) Uani 1 1 d . . . . .
H12 H 0.3758 0.2101 0.6087 0.048 Uiso 1 1 calc R U . . .
C13 C 0.3110(2) 0.32630(18) 0.7300(3) 0.0438(6) Uani 1 1 d . . . . .
H13 H 0.2322 0.2933 0.7423 0.053 Uiso 1 1 calc R U . . .
C14 C 0.3404(2) 0.42539(19) 0.7896(3) 0.0466(6) Uani 1 1 d . . . . .
H14 H 0.2820 0.4609 0.8439 0.056 Uiso 1 1 calc R U . . .
C15 C 0.4554(2) 0.47164(17) 0.7689(3) 0.0440(6) Uani 1 1 d . . . . .
H15 H 0.4737 0.5402 0.8070 0.053 Uiso 1 1 calc R U . . .
C16 C 0.5460(2) 0.42110(16) 0.6940(3) 0.0380(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2017)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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 C1 1.410(3) . ?
F2 C2 1.405(2) . ?
C1 C2 1.500(4) . ?
C1 C16 1.518(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.503(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.390(3) . ?
C3 C8 1.398(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.466(3) . ?
C9 C10 1.334(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.493(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(3) . ?
C11 C16 1.412(3) . ?
C12 C13 1.379(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(4) . ?
C15 H15 0.9500 . ?

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
F1 C1 C2 107.62(18) . . ?
F1 C1 C16 107.9(2) . . ?
C2 C1 C16 118.35(17) . . ?
F1 C1 H1 107.5 . . ?
C2 C1 H1 107.5 . . ?
C16 C1 H1 107.5 . . ?
F2 C2 C1 106.70(17) . . ?
F2 C2 C3 108.43(18) . . ?
C1 C2 C3 114.12(19) . . ?
F2 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C4 C3 C8 119.98(19) . . ?
C4 C3 C2 120.74(18) . . ?
C8 C3 C2 119.23(18) . . ?
C5 C4 C3 121.0(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 119.6(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C8 121.61(19) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 118.1(2) . . ?
C3 C8 C9 121.50(19) . . ?
C7 C8 C9 120.23(18) . . ?
C10 C9 C8 128.9(2) . . ?
C10 C9 H9 115.6 . . ?
C8 C9 H9 115.6 . . ?
C9 C10 C11 131.8(2) . . ?
C9 C10 H10 114.1 . . ?
C11 C10 H10 114.1 . . ?
C12 C11 C16 117.4(2) . . ?
C12 C11 C10 112.74(18) . . ?
C16 C11 C10 129.8(2) . . ?
C13 C12 C11 123.2(2) . . ?
C13 C12 H12 118.4 . . ?
C11 C12 H12 118.4 . . ?
C12 C13 C14 119.0(2) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 122.4(2) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C11 118.8(2) . . ?
C15 C16 C1 113.86(19) . . ?
C11 C16 C1 127.2(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 C1 C2 F2 -68.4(2) . . . . ?
C16 C1 C2 F2 169.03(17) . . . . ?
F1 C1 C2 C3 51.3(2) . . . . ?
C16 C1 C2 C3 -71.2(3) . . . . ?
F2 C2 C3 C4 32.7(3) . . . . ?
C1 C2 C3 C4 -86.0(3) . . . . ?
F2 C2 C3 C8 -144.7(2) . . . . ?
C1 C2 C3 C8 96.5(2) . . . . ?
C8 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 -177.7(2) . . . . ?
C3 C4 C5 C6 1.6(4) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 -1.5(4) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
C2 C3 C8 C7 175.7(2) . . . . ?
C4 C3 C8 C9 -177.5(2) . . . . ?
C2 C3 C8 C9 -0.1(3) . . . . ?
C6 C7 C8 C3 2.7(3) . . . . ?
C6 C7 C8 C9 178.5(2) . . . . ?
C3 C8 C9 C10 -49.5(4) . . . . ?
C7 C8 C9 C10 134.9(2) . . . . ?
C8 C9 C10 C11 -11.9(4) . . . . ?
C9 C10 C11 C12 -129.8(3) . . . . ?
C9 C10 C11 C16 50.5(4) . . . . ?
C16 C11 C12 C13 -3.6(3) . . . . ?
C10 C11 C12 C13 176.7(2) . . . . ?
C11 C12 C13 C14 2.4(3) . . . . ?
C12 C13 C14 C15 0.4(3) . . . . ?
C13 C14 C15 C16 -2.0(4) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C14 C15 C16 C1 176.9(2) . . . . ?
C12 C11 C16 C15 1.9(3) . . . . ?
C10 C11 C16 C15 -178.4(2) . . . . ?
C12 C11 C16 C1 -173.7(2) . . . . ?
C10 C11 C16 C1 5.9(4) . . . . ?
F1 C1 C16 C15 50.9(2) . . . . ?
C2 C1 C16 C15 173.25(19) . . . . ?
F1 C1 C16 C11 -133.3(2) . . . . ?
C2 C1 C16 C11 -10.9(3) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 1947541'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F2'
_chemical_formula_moiety         'C16 H12 F2'
_chemical_formula_weight         242.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      trigonal
_space_group_name_H-M_alt        R-3
_space_group_name_Hall           '-R 3'
_space_group_IT_number           148
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
#------------------------------------------------------------------------------
_cell_length_a                   35.747(2)
_cell_length_b                   35.747(2)
_cell_length_c                   4.9460(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                120.0000
_cell_volume                     5473.5(6)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    3122
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      65.72
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2268.00
_exptl_absorpt_coefficient_mu    0.804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_T_max  0.984

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device       'AFC12: Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            19054
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       43
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       5
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2212
_reflns_number_gt                1449
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).,SQUEEZE
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1392
_refine_ls_wR_factor_gt          0.1261
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2212
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0624P)²+4.5355P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.42
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.49801(4) 0.05110(5) 0.2643(3) 0.0570(5) Uani 1 1 d . . . . .
F2 F 0.53978(5) 0.00557(4) 0.2658(3) 0.0529(4) Uani 1 1 d . . . . .
C1 C 0.54267(8) 0.07217(9) 0.2450(7) 0.0561(8) Uani 1 1 d . . . . .
H1 H 0.554761 0.078208 0.432542 0.067 Uiso 1 1 calc R U . . .
C2 C 0.55556(8) 0.04377(8) 0.1139(6) 0.0529(7) Uani 1 1 d . . . . .
H2 H 0.539986 0.035244 -0.063104 0.063 Uiso 1 1 calc R U . . .
C3 C 0.60223(7) 0.05946(7) 0.0518(5) 0.0389(6) Uani 1 1 d . . . . .
C4 C 0.60813(8) 0.03606(8) -0.1532(5) 0.0446(6) Uani 1 1 d . . . . .
H4 H 0.583655 0.015167 -0.250789 0.053 Uiso 1 1 calc R U . . .
C5 C 0.64834(9) 0.04233(8) -0.2185(6) 0.0471(6) Uani 1 1 d . . . . .
H5 H 0.651489 0.026204 -0.360434 0.057 Uiso 1 1 calc R U . . .
C6 C 0.68405(8) 0.07230(9) -0.0755(6) 0.0491(7) Uani 1 1 d . . . . .
H6 H 0.711882 0.076495 -0.115610 0.059 Uiso 1 1 calc R U . . .
C7 C 0.67894(8) 0.09610(8) 0.1262(5) 0.0451(6) Uani 1 1 d . . . . .
H7 H 0.703686 0.116501 0.223878 0.054 Uiso 1 1 calc R U . . .
C8 C 0.63856(8) 0.09130(8) 0.1924(5) 0.0396(6) Uani 1 1 d . . . . .
C9 C 0.63986(8) 0.12102(8) 0.4043(5) 0.0439(6) Uani 1 1 d . . . . .
H9 H 0.654630 0.121501 0.565116 0.053 Uiso 1 1 calc R U . . .
C10 C 0.62353(8) 0.14717(8) 0.4041(5) 0.0459(6) Uani 1 1 d . . . . .
H10 H 0.630397 0.165755 0.555888 0.055 Uiso 1 1 calc R U . . .
C11 C 0.59598(8) 0.15078(8) 0.1959(5) 0.0435(6) Uani 1 1 d . . . . .
C12 C 0.60680(9) 0.19127(9) 0.0909(6) 0.0545(7) Uani 1 1 d . . . . .
H12 H 0.631644 0.216332 0.156915 0.065 Uiso 1 1 calc R U . . .
C13 C 0.58189(10) 0.19534(10) -0.1075(7) 0.0621(8) Uani 1 1 d . . . . .
H13 H 0.589831 0.223093 -0.177406 0.075 Uiso 1 1 calc R U . . .
C14 C 0.54566(10) 0.15947(11) -0.2046(6) 0.0599(8) Uani 1 1 d . . . . .
H14 H 0.529084 0.162271 -0.344932 0.072 Uiso 1 1 calc R U . . .
C15 C 0.53354(9) 0.11938(10) -0.0968(6) 0.0541(7) Uani 1 1 d . . . . .
H15 H 0.508111 0.094644 -0.160152 0.065 Uiso 1 1 calc R U . . .
C16 C 0.55830(8) 0.11498(8) 0.1037(5) 0.0438(6) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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 C1 1.387(3) . ?
F2 C2 1.406(3) . ?
C1 C2 1.460(4) . ?
C1 C16 1.512(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.502(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.396(3) . ?
C3 C8 1.410(3) . ?
C4 C5 1.378(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.404(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.477(3) . ?
C9 C10 1.327(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.474(4) . ?
C10 H10 0.9500 . ?
C11 C16 1.392(3) . ?
C11 C12 1.398(4) . ?
C12 C13 1.381(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.375(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.380(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15 0.9500 . ?

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
F1 C1 C2 109.3(2) . . ?
F1 C1 C16 108.9(2) . . ?
C2 C1 C16 114.4(2) . . ?
F1 C1 H1 108.0 . . ?
C2 C1 H1 108.0 . . ?
C16 C1 H1 108.0 . . ?
F2 C2 C1 109.0(2) . . ?
F2 C2 C3 107.7(2) . . ?
C1 C2 C3 120.6(2) . . ?
F2 C2 H2 106.3 . . ?
C1 C2 H2 106.3 . . ?
C3 C2 H2 106.3 . . ?
C4 C3 C8 119.2(2) . . ?
C4 C3 C2 113.4(2) . . ?
C8 C3 C2 127.1(2) . . ?
C5 C4 C3 122.0(2) . . ?
C5 C4 H4 119.0 . . ?
C3 C4 H4 119.0 . . ?
C4 C5 C6 119.4(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C7 C6 C5 119.5(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 122.5(2) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C3 117.3(2) . . ?
C7 C8 C9 114.6(2) . . ?
C3 C8 C9 128.0(2) . . ?
C10 C9 C8 129.8(2) . . ?
C10 C9 H9 115.1 . . ?
C8 C9 H9 115.1 . . ?
C9 C10 C11 127.7(2) . . ?
C9 C10 H10 116.2 . . ?
C11 C10 H10 116.2 . . ?
C16 C11 C12 118.0(2) . . ?
C16 C11 C10 122.0(2) . . ?
C12 C11 C10 119.9(2) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.4(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 C1 120.7(2) . . ?
C11 C16 C1 118.5(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 C1 C2 F2 -58.5(3) . . . . ?
C16 C1 C2 F2 179.1(2) . . . . ?
F1 C1 C2 C3 176.3(2) . . . . ?
C16 C1 C2 C3 53.9(4) . . . . ?
F2 C2 C3 C4 76.3(3) . . . . ?
C1 C2 C3 C4 -157.9(3) . . . . ?
F2 C2 C3 C8 -97.4(3) . . . . ?
C1 C2 C3 C8 28.4(4) . . . . ?
C8 C3 C4 C5 1.7(4) . . . . ?
C2 C3 C4 C5 -172.6(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C7 -1.4(4) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C3 2.7(4) . . . . ?
C6 C7 C8 C9 -177.2(2) . . . . ?
C4 C3 C8 C7 -3.3(3) . . . . ?
C2 C3 C8 C7 170.1(2) . . . . ?
C4 C3 C8 C9 176.5(2) . . . . ?
C2 C3 C8 C9 -10.1(4) . . . . ?
C7 C8 C9 C10 128.4(3) . . . . ?
C3 C8 C9 C10 -51.4(4) . . . . ?
C8 C9 C10 C11 5.8(5) . . . . ?
C9 C10 C11 C16 52.7(4) . . . . ?
C9 C10 C11 C12 -129.2(3) . . . . ?
C16 C11 C12 C13 -2.9(4) . . . . ?
C10 C11 C12 C13 178.9(3) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 1.9(4) . . . . ?
C13 C14 C15 C16 -1.6(4) . . . . ?
C14 C15 C16 C11 -0.9(4) . . . . ?
C14 C15 C16 C1 173.0(2) . . . . ?
C12 C11 C16 C15 3.2(4) . . . . ?
C10 C11 C16 C15 -178.6(2) . . . . ?
C12 C11 C16 C1 -170.9(2) . . . . ?
C10 C11 C16 C1 7.3(4) . . . . ?
F1 C1 C16 C15 -33.3(4) . . . . ?
C2 C1 C16 C15 89.4(3) . . . . ?
F1 C1 C16 C11 140.8(2) . . . . ?
C2 C1 C16 C11 -96.6(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.




_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: tetrahydrofuran'
####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 1947542'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-08-16 deposited with the CCDC.	2019-11-12 downloaded from the CCDC.
;
_audit_creation_date             2019-08-16
_audit_creation_method           'by CrystalStructure 4.3'

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F4'
_chemical_formula_moiety         'C16 H12 F4'
_chemical_formula_weight         280.26
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.7703(4)
_cell_length_b                   7.4822(2)
_cell_length_c                   13.8047(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 110.433(4)
_cell_angle_gamma                90.0000
_cell_volume                     1236.05(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6355
_cell_measurement_theta_min      6.84
_cell_measurement_theta_max      74.45
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576.00
_exptl_absorpt_coefficient_mu    1.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.8d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.967

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_measurement_device       'AFC11: Eulerian 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_specimen_support Loop
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13407
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_theta_max         75.587
_diffrn_reflns_theta_min         3.694
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2524
_reflns_number_gt                2191
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0625
_refine_ls_wR_factor_ref         0.1869
_refine_ls_wR_factor_gt          0.1818
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     181
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1131P)²+0.6636P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.09382(12) 0.0929(2) 0.49169(13) 0.0601(4) Uani 1 1 d . . . . .
F2 F 0.31642(15) -0.0348(2) 0.59360(13) 0.0661(5) Uani 1 1 d . . . . .
F9 F 0.30580(12) 0.4372(2) 0.77923(10) 0.0539(4) Uani 1 1 d . . . . .
F10 F 0.10848(12) 0.6089(2) 0.64317(12) 0.0589(4) Uani 1 1 d . . . . .
C1 C 0.19156(18) 0.1705(3) 0.48451(18) 0.0470(5) Uani 1 1 d . . . . .
H1 H 0.212700 0.099159 0.432898 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2838(2) 0.1444(3) 0.5893(2) 0.0529(6) Uani 1 1 d . . . . .
H2 H 0.252132 0.166723 0.644939 0.063 Uiso 1 1 calc R U . . .
C3 C 0.38247(18) 0.2653(4) 0.60640(17) 0.0487(6) Uani 1 1 d . . . . .
C4 C 0.4752(2) 0.2062(4) 0.5837(2) 0.0606(7) Uani 1 1 d . . . . .
H4 H 0.476078 0.088899 0.557651 0.073 Uiso 1 1 calc R U . . .
C5 C 0.5666(2) 0.3193(5) 0.5994(2) 0.0668(8) Uani 1 1 d . . . . .
H5 H 0.629680 0.278045 0.584438 0.080 Uiso 1 1 calc R U . . .
C6 C 0.5660(2) 0.4889(5) 0.6359(2) 0.0650(8) Uani 1 1 d . . . . .
H6 H 0.628411 0.565170 0.645964 0.078 Uiso 1 1 calc R U . . .
C7 C 0.47455(19) 0.5496(4) 0.65844(18) 0.0539(6) Uani 1 1 d . . . . .
H7 H 0.474072 0.668219 0.682777 0.065 Uiso 1 1 calc R U . . .
C8 C 0.38273(18) 0.4375(3) 0.64559(16) 0.0463(6) Uani 1 1 d . . . . .
C9 C 0.29219(19) 0.5117(3) 0.68085(17) 0.0468(5) Uani 1 1 d . . . . .
H9 H 0.304612 0.643501 0.690320 0.056 Uiso 1 1 calc R U . . .
C10 C 0.17150(19) 0.4832(3) 0.61267(18) 0.0457(5) Uani 1 1 d . . . . .
H10 H 0.147842 0.360566 0.625273 0.055 Uiso 1 1 calc R U . . .
C11 C 0.15222(16) 0.5037(3) 0.49930(16) 0.0405(5) Uani 1 1 d . . . . .
C12 C 0.12261(18) 0.6677(3) 0.45216(19) 0.0471(5) Uani 1 1 d . . . . .
H12 H 0.113419 0.766824 0.491440 0.057 Uiso 1 1 calc R U . . .
C13 C 0.10597(19) 0.6898(3) 0.34757(19) 0.0500(6) Uani 1 1 d . . . . .
H13 H 0.086996 0.803947 0.316154 0.060 Uiso 1 1 calc R U . . .
C14 C 0.11720(19) 0.5450(4) 0.28972(18) 0.0501(6) Uani 1 1 d . . . . .
H14 H 0.104947 0.558695 0.218176 0.060 Uiso 1 1 calc R U . . .
C15 C 0.14630(17) 0.3805(3) 0.33650(17) 0.0449(5) Uani 1 1 d . . . . .
H15 H 0.154013 0.281410 0.296497 0.054 Uiso 1 1 calc R U . . .
C16 C 0.16470(16) 0.3566(3) 0.44170(16) 0.0408(5) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.8d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2018/2 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# 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 C1 1.411(3) . ?
F2 C2 1.399(3) . ?
F9 C9 1.421(3) . ?
F10 C10 1.395(3) . ?
C1 C16 1.505(3) . ?
C1 C2 1.526(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.501(4) . ?
C2 H2 1.0000 . ?
C3 C8 1.397(4) . ?
C3 C4 1.399(3) . ?
C4 C5 1.396(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.508(3) . ?
C9 C10 1.515(3) . ?
C9 H9 1.0000 . ?
C10 C11 1.505(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.378(3) . ?
C11 C16 1.399(3) . ?
C12 C13 1.394(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.383(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.379(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.399(3) . ?
C15 H15 0.9500 . ?

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
F1 C1 C16 108.82(17) . . ?
F1 C1 C2 106.9(2) . . ?
C16 C1 C2 119.0(2) . . ?
F1 C1 H1 107.2 . . ?
C16 C1 H1 107.2 . . ?
C2 C1 H1 107.2 . . ?
F2 C2 C3 110.5(2) . . ?
F2 C2 C1 106.4(2) . . ?
C3 C2 C1 113.6(2) . . ?
F2 C2 H2 108.7 . . ?
C3 C2 H2 108.7 . . ?
C1 C2 H2 108.7 . . ?
C8 C3 C4 119.4(2) . . ?
C8 C3 C2 120.3(2) . . ?
C4 C3 C2 120.3(3) . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C8 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C3 C8 C7 119.3(2) . . ?
C3 C8 C9 124.5(2) . . ?
C7 C8 C9 116.1(2) . . ?
F9 C9 C8 108.18(19) . . ?
F9 C9 C10 107.27(18) . . ?
C8 C9 C10 118.42(19) . . ?
F9 C9 H9 107.5 . . ?
C8 C9 H9 107.5 . . ?
C10 C9 H9 107.5 . . ?
F10 C10 C11 110.06(19) . . ?
F10 C10 C9 106.65(18) . . ?
C11 C10 C9 113.16(18) . . ?
F10 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 H10 109.0 . . ?
C12 C11 C16 119.9(2) . . ?
C12 C11 C10 120.0(2) . . ?
C16 C11 C10 120.1(2) . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C15 C14 C13 119.6(2) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 121.3(2) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C11 C16 C15 118.6(2) . . ?
C11 C16 C1 124.1(2) . . ?
C15 C16 C1 117.3(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 C1 C2 F2 76.0(2) . . . . ?
C16 C1 C2 F2 -160.4(2) . . . . ?
F1 C1 C2 C3 -162.2(2) . . . . ?
C16 C1 C2 C3 -38.6(3) . . . . ?
F2 C2 C3 C8 -154.6(2) . . . . ?
C1 C2 C3 C8 85.9(3) . . . . ?
F2 C2 C3 C4 25.1(3) . . . . ?
C1 C2 C3 C4 -94.4(3) . . . . ?
C8 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C5 179.7(2) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C4 C3 C8 C7 1.9(3) . . . . ?
C2 C3 C8 C7 -178.4(2) . . . . ?
C4 C3 C8 C9 -175.0(2) . . . . ?
C2 C3 C8 C9 4.7(3) . . . . ?
C6 C7 C8 C3 -2.2(3) . . . . ?
C6 C7 C8 C9 175.0(2) . . . . ?
C3 C8 C9 F9 76.3(3) . . . . ?
C7 C8 C9 F9 -100.7(2) . . . . ?
C3 C8 C9 C10 -45.9(3) . . . . ?
C7 C8 C9 C10 137.1(2) . . . . ?
F9 C9 C10 F10 76.2(2) . . . . ?
C8 C9 C10 F10 -161.1(2) . . . . ?
F9 C9 C10 C11 -162.63(19) . . . . ?
C8 C9 C10 C11 -40.0(3) . . . . ?
F10 C10 C11 C12 27.5(3) . . . . ?
C9 C10 C11 C12 -91.7(2) . . . . ?
F10 C10 C11 C16 -152.67(19) . . . . ?
C9 C10 C11 C16 88.1(3) . . . . ?
C16 C11 C12 C13 -0.7(3) . . . . ?
C10 C11 C12 C13 179.08(19) . . . . ?
C11 C12 C13 C14 1.2(3) . . . . ?
C12 C13 C14 C15 -0.9(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C12 C11 C16 C15 -0.1(3) . . . . ?
C10 C11 C16 C15 -179.91(18) . . . . ?
C12 C11 C16 C1 -177.08(19) . . . . ?
C10 C11 C16 C1 3.1(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C14 C15 C16 C1 177.60(19) . . . . ?
F1 C1 C16 C11 77.0(2) . . . . ?
C2 C1 C16 C11 -45.6(3) . . . . ?
F1 C1 C16 C15 -100.0(2) . . . . ?
C2 C1 C16 C15 137.4(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/diethyl ether'
