# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1942268'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_audit_creation_date             2018-09-04
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C15 H11 F3'
_chemical_formula_moiety         'C15 H11 F3'
_chemical_formula_weight         248.25
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        P1
_space_group_name_Hall           'P 1'
_space_group_IT_number           1
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.3714(7)
_cell_length_b                   13.6749(7)
_cell_length_c                   16.1180(8)
_cell_angle_alpha                82.280(4)
_cell_angle_beta                 87.767(5)
_cell_angle_gamma                73.097(6)
_cell_volume                     1749.4(2)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2906
_cell_measurement_theta_min      5.55
_cell_measurement_theta_max      67.50
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.060
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768.00
_exptl_absorpt_coefficient_mu    0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_T_max  0.990

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            17952
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0828
_diffrn_reflns_theta_max         68.974
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.608
_diffrn_reflns_point_group_measured_fraction_full 0.623
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             7911
_reflns_number_gt                3548
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.269
_reflns_Friedel_fraction_max     0.258
_reflns_Friedel_fraction_full    0.265

#==============================================================================
# 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          0.1674
_refine_ls_R_factor_gt           0.0948
_refine_ls_wR_factor_ref         0.2782
_refine_ls_wR_factor_gt          0.2188
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         7911
_refine_ls_number_parameters     973
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1703P)²] 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         0.56
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)

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
F13 F 0.1012(7) 0.5283(4) 0.1242(4) 0.0775(15) Uani 1 1 d . . . . .
F14 F 0.3948(8) 0.3825(4) 0.1315(4) 0.0918(18) Uani 1 1 d . . . . .
F15 F 0.1975(8) 0.4261(4) -0.0071(4) 0.0865(17) Uani 1 1 d . . . . .
F33 F 0.6025(7) 0.5137(4) 0.2095(3) 0.0768(15) Uani 1 1 d . . . . .
F34 F 0.7009(7) 0.3694(4) 0.3407(4) 0.0812(16) Uani 1 1 d . . . . .
F35 F 0.8968(8) 0.3712(4) 0.2021(4) 0.0879(17) Uani 1 1 d . . . . .
F53 F 0.6243(9) -0.0484(5) 0.5435(5) 0.110(2) Uani 1 1 d . . . . .
F54 F 0.7062(10) -0.1887(5) 0.6728(5) 0.122(3) Uani 1 1 d . . . . .
F55 F 0.9166(9) -0.1897(5) 0.5407(5) 0.119(3) Uani 1 1 d . . . . .
F73 F 0.0949(8) -0.0248(4) 0.4563(4) 0.0889(18) Uani 1 1 d . . . . .
F74 F 0.3794(10) -0.1732(5) 0.4727(5) 0.120(3) Uani 1 1 d . . . . .
F75 F 0.2042(9) -0.1287(5) 0.3277(4) 0.098(2) Uani 1 1 d . . . . .
F93 F 0.1135(8) 0.0768(5) 0.7886(4) 0.0951(19) Uani 1 1 d . . . . .
F94 F 0.4088(9) -0.0649(5) 0.7920(5) 0.113(2) Uani 1 1 d . . . . .
F95 F 0.2085(9) -0.0202(5) 0.6553(5) 0.109(2) Uani 1 1 d . . . . .
F113 F 0.6028(7) 0.0675(4) 0.8762(4) 0.0875(18) Uani 1 1 d . . . . .
F114 F 0.8947(8) -0.0745(4) 0.8659(4) 0.101(2) Uani 1 1 d . . . . .
F115 F 0.7038(8) -0.0762(4) 1.0072(4) 0.095(2) Uani 1 1 d . . . . .
C1 C 0.2149(11) 0.6684(7) 0.0749(6) 0.060(2) Uani 1 1 d . . . . .
C2 C 0.1062(12) 0.7279(6) 0.1287(6) 0.066(2) Uani 1 1 d . . . . .
H2 H 0.034642 0.698899 0.164662 0.079 Uiso 1 1 calc R U . . .
C3 C 0.1028(12) 0.8299(7) 0.1294(6) 0.066(2) Uani 1 1 d . . . . .
H3 H 0.027977 0.869596 0.166379 0.080 Uiso 1 1 calc R U . . .
C4 C 0.2059(10) 0.8765(6) 0.0775(5) 0.055(2) Uani 1 1 d . . . . .
C5 C 0.3106(11) 0.8120(7) 0.0221(6) 0.069(2) Uani 1 1 d . . . . .
H5 H 0.380075 0.839848 -0.016209 0.082 Uiso 1 1 calc R U . . .
C6 C 0.3136(11) 0.7122(6) 0.0226(6) 0.067(2) Uani 1 1 d . . . . .
H6 H 0.386648 0.671828 -0.014590 0.081 Uiso 1 1 calc R U . . .
C7 C 0.2046(10) 0.9853(6) 0.0799(6) 0.059(2) Uani 1 1 d . . . . .
C8 C 0.1271(12) 1.0378(7) 0.1467(6) 0.070(2) Uani 1 1 d . . . . .
H8 H 0.072783 1.003839 0.189137 0.084 Uiso 1 1 calc R U . . .
C9 C 0.1281(13) 1.1372(8) 0.1520(7) 0.080(3) Uani 1 1 d . . . . .
H9 H 0.075153 1.171182 0.197701 0.096 Uiso 1 1 calc R U . . .
C10 C 0.2064(12) 1.1877(8) 0.0905(7) 0.076(3) Uani 1 1 d . . . . .
H10 H 0.208300 1.256107 0.094091 0.091 Uiso 1 1 calc R U . . .
C11 C 0.2821(12) 1.1375(8) 0.0238(7) 0.074(3) Uani 1 1 d . . . . .
H11 H 0.335368 1.171841 -0.018874 0.089 Uiso 1 1 calc R U . . .
C12 C 0.2801(11) 1.0386(7) 0.0192(7) 0.071(3) Uani 1 1 d . . . . .
H12 H 0.332300 1.005491 -0.027064 0.085 Uiso 1 1 calc R U . . .
C13 C 0.2234(11) 0.5576(6) 0.0780(6) 0.060(2) Uani 1 1 d . . . . .
C14 C 0.3890(13) 0.4727(7) 0.0812(6) 0.072(3) Uani 1 1 d . . . . .
H14 H 0.493008 0.495002 0.077377 0.087 Uiso 1 1 calc R U . . .
C15 C 0.2855(13) 0.4956(8) 0.0040(7) 0.075(3) Uani 1 1 d . . . . .
H15 H 0.325449 0.531541 -0.047180 0.090 Uiso 1 1 calc R U . . .
C21 C 0.7152(11) 0.6386(6) 0.2603(6) 0.059(2) Uani 1 1 d . . . . .
C22 C 0.6081(12) 0.7143(6) 0.2065(6) 0.069(3) Uani 1 1 d . . . . .
H22 H 0.539403 0.695641 0.169543 0.083 Uiso 1 1 calc R U . . .
C23 C 0.5997(12) 0.8183(7) 0.2057(7) 0.073(3) Uani 1 1 d . . . . .
H23 H 0.522957 0.869570 0.169520 0.087 Uiso 1 1 calc R U . . .
C24 C 0.7028(10) 0.8472(6) 0.2575(5) 0.0512(19) Uani 1 1 d . . . . .
C25 C 0.8060(12) 0.7689(7) 0.3121(6) 0.068(3) Uani 1 1 d . . . . .
H25 H 0.874441 0.786269 0.349979 0.081 Uiso 1 1 calc R U . . .
C26 C 0.8122(13) 0.6657(7) 0.3131(6) 0.072(3) Uani 1 1 d . . . . .
H26 H 0.884858 0.614212 0.350914 0.087 Uiso 1 1 calc R U . . .
C27 C 0.7057(10) 0.9571(6) 0.2533(6) 0.057(2) Uani 1 1 d . . . . .
C28 C 0.6206(12) 1.0311(6) 0.1896(6) 0.067(2) Uani 1 1 d . . . . .
H28 H 0.561040 1.011177 0.149030 0.081 Uiso 1 1 calc R U . . .
C29 C 0.6209(13) 1.1325(7) 0.1840(7) 0.075(3) Uani 1 1 d . . . . .
H29 H 0.563339 1.181201 0.139471 0.090 Uiso 1 1 calc R U . . .
C30 C 0.7052(12) 1.1638(8) 0.2433(7) 0.075(3) Uani 1 1 d . . . . .
H30 H 0.708440 1.233120 0.239100 0.090 Uiso 1 1 calc R U . . .
C31 C 0.7846(12) 1.0915(8) 0.3089(7) 0.072(3) Uani 1 1 d . . . . .
H31 H 0.841331 1.111792 0.350479 0.087 Uiso 1 1 calc R U . . .
C32 C 0.7820(12) 0.9901(7) 0.3143(7) 0.070(2) Uani 1 1 d . . . . .
H32 H 0.833452 0.942334 0.360740 0.084 Uiso 1 1 calc R U . . .
C33 C 0.7226(11) 0.5286(6) 0.2566(6) 0.057(2) Uani 1 1 d . . . . .
C34 C 0.7838(13) 0.4433(7) 0.3294(6) 0.069(2) Uani 1 1 d . . . . .
H34 H 0.822655 0.463166 0.380887 0.083 Uiso 1 1 calc R U . . .
C35 C 0.8898(13) 0.4444(7) 0.2537(6) 0.072(3) Uani 1 1 d . . . . .
H35 H 0.993539 0.465499 0.258648 0.087 Uiso 1 1 calc R U . . .
C41 C 0.7285(12) 0.0779(8) 0.5937(7) 0.070(3) Uani 1 1 d . . . . .
C42 C 0.6517(14) 0.1496(7) 0.5291(7) 0.081(3) Uani 1 1 d . . . . .
H42 H 0.604681 0.128118 0.484634 0.097 Uiso 1 1 calc R U . . .
C43 C 0.6410(13) 0.2534(7) 0.5271(6) 0.071(3) Uani 1 1 d . . . . .
H43 H 0.584643 0.301706 0.482049 0.085 Uiso 1 1 calc R U . . .
C44 C 0.7122(11) 0.2874(7) 0.5907(6) 0.060(2) Uani 1 1 d . . . . .
C45 C 0.7876(12) 0.2144(7) 0.6560(6) 0.069(2) Uani 1 1 d . . . . .
H45 H 0.836292 0.235633 0.700024 0.082 Uiso 1 1 calc R U . . .
C46 C 0.7949(15) 0.1132(8) 0.6598(7) 0.085(3) Uani 1 1 d . . . . .
H46 H 0.844734 0.065911 0.706826 0.102 Uiso 1 1 calc R U . . .
C47 C 0.7051(10) 0.4003(6) 0.5871(6) 0.058(2) Uani 1 1 d . . . . .
C48 C 0.6044(12) 0.4765(7) 0.5277(6) 0.074(3) Uani 1 1 d . . . . .
H48 H 0.536310 0.458338 0.490151 0.089 Uiso 1 1 calc R U . . .
C49 C 0.6061(13) 0.5810(7) 0.5246(7) 0.078(3) Uani 1 1 d . . . . .
H49 H 0.539549 0.631541 0.483824 0.094 Uiso 1 1 calc R U . . .
C50 C 0.6991(12) 0.6106(8) 0.5777(7) 0.073(3) Uani 1 1 d . . . . .
H50 H 0.699775 0.680389 0.573655 0.087 Uiso 1 1 calc R U . . .
C51 C 0.7924(13) 0.5376(8) 0.6375(7) 0.078(3) Uani 1 1 d . . . . .
H51 H 0.856391 0.557391 0.676130 0.094 Uiso 1 1 calc R U . . .
C52 C 0.7944(13) 0.4353(8) 0.6423(7) 0.081(3) Uani 1 1 d . . . . .
H52 H 0.859272 0.386893 0.684867 0.097 Uiso 1 1 calc R U . . .
C53 C 0.7428(14) -0.0340(8) 0.5927(7) 0.076(3) Uani 1 1 d . . . . .
C54 C 0.7938(15) -0.1168(8) 0.6642(7) 0.086(3) Uani 1 1 d . . . . .
H54 H 0.826998 -0.096811 0.716918 0.103 Uiso 1 1 calc R U . . .
C55 C 0.9058(16) -0.1157(8) 0.5929(7) 0.095(3) Uani 1 1 d . . . . .
H55 H 1.009131 -0.095367 0.600850 0.113 Uiso 1 1 calc R U . . .
C61 C 0.2167(13) 0.1108(7) 0.4127(6) 0.069(3) Uani 1 1 d . . . . .
C62 C 0.1020(12) 0.1731(7) 0.4635(6) 0.069(2) Uani 1 1 d . . . . .
H62 H 0.025892 0.146163 0.497865 0.083 Uiso 1 1 calc R U . . .
C63 C 0.1015(12) 0.2777(7) 0.4628(6) 0.067(2) Uani 1 1 d . . . . .
H63 H 0.023802 0.319996 0.497100 0.080 Uiso 1 1 calc R U . . .
C64 C 0.2106(11) 0.3190(6) 0.4138(6) 0.059(2) Uani 1 1 d . . . . .
C65 C 0.3212(12) 0.2546(7) 0.3636(6) 0.072(3) Uani 1 1 d . . . . .
H65 H 0.395675 0.282007 0.328291 0.086 Uiso 1 1 calc R U . . .
C66 C 0.3269(12) 0.1534(8) 0.3630(7) 0.076(3) Uani 1 1 d . . . . .
H66 H 0.406100 0.112001 0.328758 0.092 Uiso 1 1 calc R U . . .
C67 C 0.2074(11) 0.4292(7) 0.4146(6) 0.064(2) Uani 1 1 d . . . . .
C68 C 0.1350(12) 0.4801(7) 0.4811(7) 0.073(3) Uani 1 1 d . . . . .
H68 H 0.086922 0.445770 0.525978 0.088 Uiso 1 1 calc R U . . .
C69 C 0.1329(12) 0.5852(8) 0.4820(7) 0.078(3) Uani 1 1 d . . . . .
H69 H 0.081968 0.620273 0.527543 0.094 Uiso 1 1 calc R U . . .
C70 C 0.2030(14) 0.6360(8) 0.4183(8) 0.079(3) Uani 1 1 d . . . . .
H70 H 0.203049 0.705127 0.419984 0.095 Uiso 1 1 calc R U . . .
C71 C 0.2743(12) 0.5841(7) 0.3507(7) 0.077(3) Uani 1 1 d . . . . .
H71 H 0.323113 0.618726 0.306275 0.092 Uiso 1 1 calc R U . . .
C72 C 0.2753(12) 0.4830(7) 0.3474(7) 0.075(3) Uani 1 1 d . . . . .
H72 H 0.321370 0.449736 0.300210 0.090 Uiso 1 1 calc R U . . .
C73 C 0.2231(13) 0.0010(7) 0.4153(6) 0.068(2) Uani 1 1 d . . . . .
C74 C 0.3834(15) -0.0857(7) 0.4222(8) 0.093(4) Uani 1 1 d . . . . .
H74 H 0.489436 -0.065887 0.421612 0.112 Uiso 1 1 calc R U . . .
C75 C 0.2921(13) -0.0631(8) 0.3442(7) 0.074(3) Uani 1 1 d . . . . .
H75 H 0.340665 -0.028781 0.294977 0.089 Uiso 1 1 calc R U . . .
C81 C 0.2198(10) 0.2194(7) 0.7415(6) 0.064(2) Uani 1 1 d . . . . .
C82 C 0.1304(13) 0.2726(8) 0.8044(6) 0.078(3) Uani 1 1 d . . . . .
H82 H 0.075283 0.238367 0.846179 0.094 Uiso 1 1 calc R U . . .
C83 C 0.1210(12) 0.3770(8) 0.8065(6) 0.077(3) Uani 1 1 d . . . . .
H83 H 0.055530 0.413078 0.848338 0.092 Uiso 1 1 calc R U . . .
C84 C 0.2058(11) 0.4277(6) 0.7483(6) 0.057(2) Uani 1 1 d . . . . .
C85 C 0.2955(13) 0.3716(7) 0.6857(6) 0.071(3) Uani 1 1 d . . . . .
H85 H 0.352859 0.404688 0.644207 0.086 Uiso 1 1 calc R U . . .
C86 C 0.3023(13) 0.2728(8) 0.6830(6) 0.078(3) Uani 1 1 d . . . . .
H86 H 0.365304 0.237959 0.639906 0.093 Uiso 1 1 calc R U . . .
C87 C 0.2043(11) 0.5368(7) 0.7511(6) 0.063(2) Uani 1 1 d . . . . .
C88 C 0.1012(14) 0.5964(8) 0.8067(7) 0.085(3) Uani 1 1 d . . . . .
H88 H 0.028408 0.567289 0.841678 0.102 Uiso 1 1 calc R U . . .
C89 C 0.1008(14) 0.6997(9) 0.8131(8) 0.094(3) Uani 1 1 d . . . . .
H89 H 0.030776 0.736963 0.853003 0.113 Uiso 1 1 calc R U . . .
C90 C 0.2004(14) 0.7453(9) 0.7621(8) 0.081(3) Uani 1 1 d . . . . .
H90 H 0.202976 0.813473 0.766150 0.098 Uiso 1 1 calc R U . . .
C91 C 0.3006(15) 0.6856(8) 0.7023(8) 0.093(3) Uani 1 1 d . . . . .
H91 H 0.367121 0.715656 0.663723 0.112 Uiso 1 1 calc R U . . .
C92 C 0.3016(14) 0.5869(8) 0.7001(7) 0.084(3) Uani 1 1 d . . . . .
H92 H 0.373681 0.549341 0.661006 0.101 Uiso 1 1 calc R U . . .
C93 C 0.2313(13) 0.1081(7) 0.7422(7) 0.072(3) Uani 1 1 d . . . . .
C94 C 0.3986(15) 0.0254(7) 0.7412(7) 0.088(3) Uani 1 1 d . . . . .
H94 H 0.501093 0.049340 0.736117 0.105 Uiso 1 1 calc R U . . .
C95 C 0.2911(14) 0.0501(8) 0.6682(7) 0.079(3) Uani 1 1 d . . . . .
H95 H 0.326725 0.089041 0.617379 0.095 Uiso 1 1 calc R U . . .
C101 C 0.7175(11) 0.1911(7) 0.9258(6) 0.064(2) Uani 1 1 d . . . . .
C102 C 0.6061(12) 0.2677(6) 0.8730(6) 0.072(3) Uani 1 1 d . . . . .
H102 H 0.532256 0.251093 0.837568 0.086 Uiso 1 1 calc R U . . .
C103 C 0.6065(13) 0.3718(7) 0.8738(7) 0.073(3) Uani 1 1 d . . . . .
H103 H 0.531287 0.424664 0.838114 0.087 Uiso 1 1 calc R U . . .
C104 C 0.7101(12) 0.3984(6) 0.9236(6) 0.059(2) Uani 1 1 d . . . . .
C105 C 0.8188(12) 0.3187(7) 0.9773(6) 0.069(3) Uani 1 1 d . . . . .
H105 H 0.891607 0.334936 1.013454 0.083 Uiso 1 1 calc R U . . .
C106 C 0.8204(12) 0.2190(7) 0.9777(7) 0.074(3) Uani 1 1 d . . . . .
H106 H 0.894147 0.166912 1.014626 0.089 Uiso 1 1 calc R U . . .
C107 C 0.7083(11) 0.5088(7) 0.9244(6) 0.066(2) Uani 1 1 d . . . . .
C108 C 0.6413(13) 0.5820(7) 0.8556(6) 0.074(3) Uani 1 1 d . . . . .
H108 H 0.597043 0.560911 0.809971 0.089 Uiso 1 1 calc R U . . .
C109 C 0.6380(14) 0.6860(8) 0.8525(8) 0.082(3) Uani 1 1 d . . . . .
H109 H 0.591546 0.734152 0.805309 0.098 Uiso 1 1 calc R U . . .
C110 C 0.7026(15) 0.7180(9) 0.9183(8) 0.087(3) Uani 1 1 d . . . . .
H110 H 0.700730 0.787989 0.916715 0.104 Uiso 1 1 calc R U . . .
C111 C 0.7718(13) 0.6450(8) 0.9883(8) 0.081(3) Uani 1 1 d . . . . .
H111 H 0.817240 0.665894 1.033653 0.097 Uiso 1 1 calc R U . . .
C112 C 0.7729(13) 0.5438(8) 0.9902(7) 0.076(3) Uani 1 1 d . . . . .
H112 H 0.818906 0.495908 1.037583 0.092 Uiso 1 1 calc R U . . .
C113 C 0.7286(12) 0.0809(7) 0.9219(6) 0.064(2) Uani 1 1 d . . . . .
C114 C 0.8923(14) -0.0017(7) 0.9189(6) 0.079(3) Uani 1 1 d . . . . .
H114 H 0.996878 0.018531 0.923428 0.095 Uiso 1 1 calc R U . . .
C115 C 0.7879(12) -0.0024(7) 0.9930(7) 0.074(3) Uani 1 1 d . . . . .
H115 H 0.827639 0.018300 1.043840 0.088 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14a (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT Version 2014/4 (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
F13 C13 1.364(10) . ?
F14 C14 1.372(10) . ?
F15 C15 1.394(10) . ?
F33 C33 1.360(10) . ?
F34 C34 1.373(10) . ?
F35 C35 1.373(10) . ?
F53 C53 1.367(12) . ?
F54 C54 1.378(12) . ?
F55 C55 1.381(11) . ?
F73 C73 1.348(11) . ?
F74 C74 1.362(11) . ?
F75 C75 1.371(10) . ?
F93 C93 1.348(11) . ?
F94 C94 1.369(11) . ?
F95 C95 1.378(11) . ?
F113 C113 1.376(10) . ?
F114 C114 1.392(10) . ?
F115 C115 1.379(10) . ?
C1 C6 1.361(12) . ?
C1 C2 1.392(12) . ?
C1 C13 1.490(11) . ?
C2 C3 1.388(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(12) . ?
C3 H3 0.9500 . ?
C4 C5 1.430(12) . ?
C4 C7 1.490(11) . ?
C5 C6 1.356(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.384(12) . ?
C7 C8 1.407(13) . ?
C8 C9 1.377(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.370(13) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.525(12) . ?
C13 C15 1.541(13) . ?
C14 C15 1.489(14) . ?
C14 H14 1.0000 . ?
C15 H15 1.0000 . ?
C21 C26 1.355(12) . ?
C21 C22 1.380(12) . ?
C21 C33 1.497(11) . ?
C22 C23 1.402(12) . ?
C22 H22 0.9500 . ?
C23 C24 1.393(11) . ?
C23 H23 0.9500 . ?
C24 C25 1.391(11) . ?
C24 C27 1.503(10) . ?
C25 C26 1.394(12) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.384(13) . ?
C27 C28 1.395(12) . ?
C28 C29 1.378(12) . ?
C28 H28 0.9500 . ?
C29 C30 1.391(15) . ?
C29 H29 0.9500 . ?
C30 C31 1.389(14) . ?
C30 H30 0.9500 . ?
C31 C32 1.384(13) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C34 1.528(12) . ?
C33 C35 1.536(12) . ?
C34 C35 1.482(13) . ?
C34 H34 1.0000 . ?
C35 H35 1.0000 . ?
C41 C42 1.368(13) . ?
C41 C46 1.419(14) . ?
C41 C53 1.502(13) . ?
C42 C43 1.392(12) . ?
C42 H42 0.9500 . ?
C43 C44 1.400(13) . ?
C43 H43 0.9500 . ?
C44 C45 1.380(12) . ?
C44 C47 1.520(11) . ?
C45 C46 1.360(13) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C47 C52 1.398(13) . ?
C47 C48 1.414(12) . ?
C48 C49 1.427(13) . ?
C48 H48 0.9500 . ?
C49 C50 1.353(14) . ?
C49 H49 0.9500 . ?
C50 C51 1.372(14) . ?
C50 H50 0.9500 . ?
C51 C52 1.386(13) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.483(14) . ?
C53 C55 1.491(15) . ?
C54 C55 1.456(15) . ?
C54 H54 1.0000 . ?
C55 H55 1.0000 . ?
C61 C66 1.401(13) . ?
C61 C62 1.404(13) . ?
C61 C73 1.482(12) . ?
C62 C63 1.427(12) . ?
C62 H62 0.9500 . ?
C63 C64 1.379(12) . ?
C63 H63 0.9500 . ?
C64 C65 1.396(12) . ?
C64 C67 1.500(11) . ?
C65 C66 1.372(13) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 C68 1.380(13) . ?
C67 C72 1.421(13) . ?
C68 C69 1.434(12) . ?
C68 H68 0.9500 . ?
C69 C70 1.371(15) . ?
C69 H69 0.9500 . ?
C70 C71 1.398(16) . ?
C70 H70 0.9500 . ?
C71 C72 1.389(13) . ?
C71 H71 0.9500 . ?
C72 H72 0.9500 . ?
C73 C74 1.506(14) . ?
C73 C75 1.530(14) . ?
C74 C75 1.448(15) . ?
C74 H74 1.0000 . ?
C75 H75 1.0000 . ?
C81 C82 1.392(13) . ?
C81 C86 1.399(13) . ?
C81 C93 1.496(12) . ?
C82 C83 1.412(13) . ?
C82 H82 0.9500 . ?
C83 C84 1.387(12) . ?
C83 H83 0.9500 . ?
C84 C85 1.408(13) . ?
C84 C87 1.495(12) . ?
C85 C86 1.342(13) . ?
C85 H85 0.9500 . ?
C86 H86 0.9500 . ?
C87 C92 1.389(13) . ?
C87 C88 1.393(14) . ?
C88 C89 1.429(15) . ?
C88 H88 0.9500 . ?
C89 C90 1.368(16) . ?
C89 H89 0.9500 . ?
C90 C91 1.431(16) . ?
C90 H90 0.9500 . ?
C91 C92 1.352(14) . ?
C91 H91 0.9500 . ?
C92 H92 0.9500 . ?
C93 C95 1.508(14) . ?
C93 C94 1.524(14) . ?
C94 C95 1.451(15) . ?
C94 H94 1.0000 . ?
C95 H95 1.0000 . ?
C101 C106 1.386(13) . ?
C101 C102 1.396(12) . ?
C101 C113 1.492(12) . ?
C102 C103 1.427(12) . ?
C102 H102 0.9500 . ?
C103 C104 1.358(13) . ?
C103 H103 0.9500 . ?
C104 C105 1.413(12) . ?
C104 C107 1.507(12) . ?
C105 C106 1.358(12) . ?
C105 H105 0.9500 . ?
C106 H106 0.9500 . ?
C107 C108 1.403(13) . ?
C107 C112 1.406(14) . ?
C108 C109 1.409(13) . ?
C108 H108 0.9500 . ?
C109 C110 1.384(17) . ?
C109 H109 0.9500 . ?
C110 C111 1.419(16) . ?
C110 H110 0.9500 . ?
C111 C112 1.378(14) . ?
C111 H111 0.9500 . ?
C112 H112 0.9500 . ?
C113 C115 1.491(13) . ?
C113 C114 1.505(13) . ?
C114 C115 1.453(14) . ?
C114 H114 1.0000 . ?
C115 H115 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
C6 C1 C2 119.1(8) . . ?
C6 C1 C13 121.8(8) . . ?
C2 C1 C13 119.1(8) . . ?
C3 C2 C1 119.7(8) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 122.4(8) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 114.9(8) . . ?
C3 C4 C7 122.2(8) . . ?
C5 C4 C7 122.9(8) . . ?
C6 C5 C4 122.0(8) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C1 121.8(8) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
C12 C7 C8 117.0(8) . . ?
C12 C7 C4 122.9(9) . . ?
C8 C7 C4 120.1(8) . . ?
C9 C8 C7 121.4(9) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.9(10) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C11 119.5(10) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 120.1(10) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 122.1(10) . . ?
C11 C12 H12 118.9 . . ?
C7 C12 H12 118.9 . . ?
F13 C13 C1 115.0(7) . . ?
F13 C13 C14 113.0(7) . . ?
C1 C13 C14 122.2(8) . . ?
F13 C13 C15 113.8(7) . . ?
C1 C13 C15 123.0(8) . . ?
C14 C13 C15 58.1(6) . . ?
F14 C14 C15 116.5(8) . . ?
F14 C14 C13 116.6(8) . . ?
C15 C14 C13 61.5(6) . . ?
F14 C14 H14 116.9 . . ?
C15 C14 H14 116.9 . . ?
C13 C14 H14 116.9 . . ?
F15 C15 C14 116.6(9) . . ?
F15 C15 C13 114.1(8) . . ?
C14 C15 C13 60.4(6) . . ?
F15 C15 H15 117.7 . . ?
C14 C15 H15 117.7 . . ?
C13 C15 H15 117.7 . . ?
C26 C21 C22 119.4(8) . . ?
C26 C21 C33 122.2(8) . . ?
C22 C21 C33 118.4(8) . . ?
C21 C22 C23 120.7(8) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 120.7(8) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 116.8(8) . . ?
C23 C24 C27 121.8(7) . . ?
C25 C24 C27 121.5(7) . . ?
C24 C25 C26 122.1(8) . . ?
C24 C25 H25 119.0 . . ?
C26 C25 H25 119.0 . . ?
C21 C26 C25 120.3(8) . . ?
C21 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C32 C27 C28 117.6(8) . . ?
C32 C27 C24 122.1(8) . . ?
C28 C27 C24 120.2(8) . . ?
C29 C28 C27 121.6(9) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C28 C29 C30 120.2(10) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C31 C30 C29 118.6(9) . . ?
C31 C30 H30 120.7 . . ?
C29 C30 H30 120.7 . . ?
C32 C31 C30 120.6(10) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C27 C32 C31 121.2(9) . . ?
C27 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
F33 C33 C21 115.7(7) . . ?
F33 C33 C34 113.6(7) . . ?
C21 C33 C34 123.0(8) . . ?
F33 C33 C35 112.7(7) . . ?
C21 C33 C35 121.5(8) . . ?
C34 C33 C35 57.8(6) . . ?
F34 C34 C35 116.6(8) . . ?
F34 C34 C33 115.5(8) . . ?
C35 C34 C33 61.4(6) . . ?
F34 C34 H34 117.2 . . ?
C35 C34 H34 117.2 . . ?
C33 C34 H34 117.2 . . ?
F35 C35 C34 117.1(8) . . ?
F35 C35 C33 116.3(8) . . ?
C34 C35 C33 60.8(6) . . ?
F35 C35 H35 116.9 . . ?
C34 C35 H35 116.9 . . ?
C33 C35 H35 116.9 . . ?
C42 C41 C46 117.6(9) . . ?
C42 C41 C53 120.2(10) . . ?
C46 C41 C53 122.2(9) . . ?
C41 C42 C43 121.5(10) . . ?
C41 C42 H42 119.2 . . ?
C43 C42 H42 119.2 . . ?
C42 C43 C44 120.7(9) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C45 C44 C43 117.1(8) . . ?
C45 C44 C47 122.2(8) . . ?
C43 C44 C47 120.7(8) . . ?
C46 C45 C44 122.7(9) . . ?
C46 C45 H45 118.6 . . ?
C44 C45 H45 118.6 . . ?
C45 C46 C41 120.2(10) . . ?
C45 C46 H46 119.9 . . ?
C41 C46 H46 119.9 . . ?
C52 C47 C48 116.0(8) . . ?
C52 C47 C44 122.7(8) . . ?
C48 C47 C44 121.3(8) . . ?
C47 C48 C49 119.4(9) . . ?
C47 C48 H48 120.3 . . ?
C49 C48 H48 120.3 . . ?
C50 C49 C48 122.3(9) . . ?
C50 C49 H49 118.9 . . ?
C48 C49 H49 118.9 . . ?
C49 C50 C51 118.6(9) . . ?
C49 C50 H50 120.7 . . ?
C51 C50 H50 120.7 . . ?
C50 C51 C52 120.7(10) . . ?
C50 C51 H51 119.6 . . ?
C52 C51 H51 119.6 . . ?
C51 C52 C47 122.9(9) . . ?
C51 C52 H52 118.6 . . ?
C47 C52 H52 118.6 . . ?
F53 C53 C54 112.6(9) . . ?
F53 C53 C55 113.6(9) . . ?
C54 C53 C55 58.6(7) . . ?
F53 C53 C41 112.7(8) . . ?
C54 C53 C41 125.9(10) . . ?
C55 C53 C41 123.3(10) . . ?
F54 C54 C55 118.0(10) . . ?
F54 C54 C53 115.4(10) . . ?
C55 C54 C53 61.0(7) . . ?
F54 C54 H54 116.9 . . ?
C55 C54 H54 116.9 . . ?
C53 C54 H54 116.9 . . ?
F55 C55 C54 115.9(10) . . ?
F55 C55 C53 115.9(10) . . ?
C54 C55 C53 60.4(7) . . ?
F55 C55 H55 117.4 . . ?
C54 C55 H55 117.4 . . ?
C53 C55 H55 117.4 . . ?
C66 C61 C62 118.8(9) . . ?
C66 C61 C73 121.6(9) . . ?
C62 C61 C73 119.5(9) . . ?
C61 C62 C63 118.9(9) . . ?
C61 C62 H62 120.5 . . ?
C63 C62 H62 120.5 . . ?
C64 C63 C62 121.9(8) . . ?
C64 C63 H63 119.0 . . ?
C62 C63 H63 119.0 . . ?
C63 C64 C65 117.2(8) . . ?
C63 C64 C67 120.7(8) . . ?
C65 C64 C67 122.1(9) . . ?
C66 C65 C64 122.7(9) . . ?
C66 C65 H65 118.7 . . ?
C64 C65 H65 118.7 . . ?
C65 C66 C61 120.4(9) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?
C68 C67 C72 119.1(9) . . ?
C68 C67 C64 119.7(9) . . ?
C72 C67 C64 121.2(9) . . ?
C67 C68 C69 119.6(10) . . ?
C67 C68 H68 120.2 . . ?
C69 C68 H68 120.2 . . ?
C70 C69 C68 121.2(10) . . ?
C70 C69 H69 119.4 . . ?
C68 C69 H69 119.4 . . ?
C69 C70 C71 118.8(10) . . ?
C69 C70 H70 120.6 . . ?
C71 C70 H70 120.6 . . ?
C72 C71 C70 121.2(10) . . ?
C72 C71 H71 119.4 . . ?
C70 C71 H71 119.4 . . ?
C71 C72 C67 120.0(10) . . ?
C71 C72 H72 120.0 . . ?
C67 C72 H72 120.0 . . ?
F73 C73 C61 114.4(8) . . ?
F73 C73 C74 113.1(8) . . ?
C61 C73 C74 123.3(9) . . ?
F73 C73 C75 113.3(8) . . ?
C61 C73 C75 123.7(9) . . ?
C74 C73 C75 57.0(7) . . ?
F74 C74 C75 116.9(10) . . ?
F74 C74 C73 116.2(10) . . ?
C75 C74 C73 62.3(7) . . ?
F74 C74 H74 116.8 . . ?
C75 C74 H74 116.8 . . ?
C73 C74 H74 116.8 . . ?
F75 C75 C74 118.1(9) . . ?
F75 C75 C73 115.3(9) . . ?
C74 C75 C73 60.7(7) . . ?
F75 C75 H75 116.9 . . ?
C74 C75 H75 116.9 . . ?
C73 C75 H75 116.9 . . ?
C82 C81 C86 117.2(9) . . ?
C82 C81 C93 119.3(9) . . ?
C86 C81 C93 123.4(9) . . ?
C81 C82 C83 120.5(9) . . ?
C81 C82 H82 119.7 . . ?
C83 C82 H82 119.7 . . ?
C84 C83 C82 121.0(9) . . ?
C84 C83 H83 119.5 . . ?
C82 C83 H83 119.5 . . ?
C83 C84 C85 117.1(8) . . ?
C83 C84 C87 122.2(9) . . ?
C85 C84 C87 120.7(8) . . ?
C86 C85 C84 121.9(9) . . ?
C86 C85 H85 119.1 . . ?
C84 C85 H85 119.1 . . ?
C85 C86 C81 122.3(10) . . ?
C85 C86 H86 118.9 . . ?
C81 C86 H86 118.9 . . ?
C92 C87 C88 114.8(9) . . ?
C92 C87 C84 124.2(9) . . ?
C88 C87 C84 121.0(9) . . ?
C87 C88 C89 122.5(11) . . ?
C87 C88 H88 118.7 . . ?
C89 C88 H88 118.7 . . ?
C90 C89 C88 120.5(11) . . ?
C90 C89 H89 119.8 . . ?
C88 C89 H89 119.8 . . ?
C89 C90 C91 117.0(11) . . ?
C89 C90 H90 121.5 . . ?
C91 C90 H90 121.5 . . ?
C92 C91 C90 120.7(11) . . ?
C92 C91 H91 119.7 . . ?
C90 C91 H91 119.7 . . ?
C91 C92 C87 124.5(11) . . ?
C91 C92 H92 117.8 . . ?
C87 C92 H92 117.8 . . ?
F93 C93 C81 114.5(8) . . ?
F93 C93 C95 114.2(9) . . ?
C81 C93 C95 123.2(9) . . ?
F93 C93 C94 113.9(8) . . ?
C81 C93 C94 121.9(9) . . ?
C95 C93 C94 57.2(7) . . ?
F94 C94 C95 117.8(10) . . ?
F94 C94 C93 115.4(10) . . ?
C95 C94 C93 60.9(7) . . ?
F94 C94 H94 117.0 . . ?
C95 C94 H94 117.0 . . ?
C93 C94 H94 117.0 . . ?
F95 C95 C94 117.0(10) . . ?
F95 C95 C93 115.3(9) . . ?
C94 C95 C93 62.0(7) . . ?
F95 C95 H95 117.0 . . ?
C94 C95 H95 117.0 . . ?
C93 C95 H95 117.0 . . ?
C106 C101 C102 119.1(8) . . ?
C106 C101 C113 121.7(8) . . ?
C102 C101 C113 119.1(9) . . ?
C101 C102 C103 117.8(9) . . ?
C101 C102 H102 121.1 . . ?
C103 C102 H102 121.1 . . ?
C104 C103 C102 122.7(9) . . ?
C104 C103 H103 118.6 . . ?
C102 C103 H103 118.6 . . ?
C103 C104 C105 117.6(8) . . ?
C103 C104 C107 122.1(8) . . ?
C105 C104 C107 120.2(9) . . ?
C106 C105 C104 120.7(9) . . ?
C106 C105 H105 119.6 . . ?
C104 C105 H105 119.6 . . ?
C105 C106 C101 121.9(9) . . ?
C105 C106 H106 119.0 . . ?
C101 C106 H106 119.0 . . ?
C108 C107 C112 117.0(9) . . ?
C108 C107 C104 119.3(9) . . ?
C112 C107 C104 123.7(9) . . ?
C107 C108 C109 121.7(10) . . ?
C107 C108 H108 119.1 . . ?
C109 C108 H108 119.1 . . ?
C110 C109 C108 119.9(10) . . ?
C110 C109 H109 120.1 . . ?
C108 C109 H109 120.1 . . ?
C109 C110 C111 119.3(11) . . ?
C109 C110 H110 120.3 . . ?
C111 C110 H110 120.3 . . ?
C112 C111 C110 119.8(11) . . ?
C112 C111 H111 120.1 . . ?
C110 C111 H111 120.1 . . ?
C111 C112 C107 122.3(10) . . ?
C111 C112 H112 118.9 . . ?
C107 C112 H112 118.9 . . ?
F113 C113 C115 113.4(7) . . ?
F113 C113 C101 113.9(8) . . ?
C115 C113 C101 123.3(9) . . ?
F113 C113 C114 114.3(7) . . ?
C115 C113 C114 58.0(6) . . ?
C101 C113 C114 122.8(8) . . ?
F114 C114 C115 116.6(9) . . ?
F114 C114 C113 114.8(8) . . ?
C115 C114 C113 60.5(7) . . ?
F114 C114 H114 117.5 . . ?
C115 C114 H114 117.5 . . ?
C113 C114 H114 117.5 . . ?
F115 C115 C114 118.4(9) . . ?
F115 C115 C113 116.9(8) . . ?
C114 C115 C113 61.5(7) . . ?
F115 C115 H115 116.3 . . ?
C114 C115 H115 116.3 . . ?
C113 C115 H115 116.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.4(14) . . . . ?
C13 C1 C2 C3 176.9(9) . . . . ?
C1 C2 C3 C4 0.0(14) . . . . ?
C2 C3 C4 C5 1.9(13) . . . . ?
C2 C3 C4 C7 -178.6(9) . . . . ?
C3 C4 C5 C6 -2.5(13) . . . . ?
C7 C4 C5 C6 178.0(9) . . . . ?
C4 C5 C6 C1 1.2(15) . . . . ?
C2 C1 C6 C5 0.8(14) . . . . ?
C13 C1 C6 C5 -177.4(9) . . . . ?
C3 C4 C7 C12 -167.3(9) . . . . ?
C5 C4 C7 C12 12.2(13) . . . . ?
C3 C4 C7 C8 14.0(12) . . . . ?
C5 C4 C7 C8 -166.5(9) . . . . ?
C12 C7 C8 C9 -0.8(13) . . . . ?
C4 C7 C8 C9 178.0(8) . . . . ?
C7 C8 C9 C10 0.1(15) . . . . ?
C8 C9 C10 C11 0.5(15) . . . . ?
C9 C10 C11 C12 -0.5(15) . . . . ?
C10 C11 C12 C7 -0.2(15) . . . . ?
C8 C7 C12 C11 0.8(13) . . . . ?
C4 C7 C12 C11 -178.0(8) . . . . ?
C6 C1 C13 F13 -171.0(8) . . . . ?
C2 C1 C13 F13 10.7(12) . . . . ?
C6 C1 C13 C14 45.7(13) . . . . ?
C2 C1 C13 C14 -132.5(9) . . . . ?
C6 C1 C13 C15 -24.6(14) . . . . ?
C2 C1 C13 C15 157.1(9) . . . . ?
F13 C13 C14 F14 -2.6(11) . . . . ?
C1 C13 C14 F14 141.3(9) . . . . ?
C15 C13 C14 F14 -107.2(9) . . . . ?
F13 C13 C14 C15 104.6(9) . . . . ?
C1 C13 C14 C15 -111.5(10) . . . . ?
F14 C14 C15 F15 3.4(13) . . . . ?
C13 C14 C15 F15 -104.0(9) . . . . ?
F14 C14 C15 C13 107.4(9) . . . . ?
F13 C13 C15 F15 4.9(12) . . . . ?
C1 C13 C15 F15 -141.9(9) . . . . ?
C14 C13 C15 F15 108.0(10) . . . . ?
F13 C13 C15 C14 -103.2(9) . . . . ?
C1 C13 C15 C14 110.1(10) . . . . ?
C26 C21 C22 C23 0.3(15) . . . . ?
C33 C21 C22 C23 -178.2(9) . . . . ?
C21 C22 C23 C24 1.9(15) . . . . ?
C22 C23 C24 C25 -3.3(14) . . . . ?
C22 C23 C24 C27 175.3(9) . . . . ?
C23 C24 C25 C26 2.6(14) . . . . ?
C27 C24 C25 C26 -175.9(9) . . . . ?
C22 C21 C26 C25 -1.0(15) . . . . ?
C33 C21 C26 C25 177.5(9) . . . . ?
C24 C25 C26 C21 -0.5(15) . . . . ?
C23 C24 C27 C32 167.3(9) . . . . ?
C25 C24 C27 C32 -14.2(13) . . . . ?
C23 C24 C27 C28 -8.4(12) . . . . ?
C25 C24 C27 C28 170.1(9) . . . . ?
C32 C27 C28 C29 4.1(13) . . . . ?
C24 C27 C28 C29 -180.0(9) . . . . ?
C27 C28 C29 C30 -0.9(14) . . . . ?
C28 C29 C30 C31 -1.6(15) . . . . ?
C29 C30 C31 C32 1.0(15) . . . . ?
C28 C27 C32 C31 -4.8(14) . . . . ?
C24 C27 C32 C31 179.4(8) . . . . ?
C30 C31 C32 C27 2.3(15) . . . . ?
C26 C21 C33 F33 171.1(9) . . . . ?
C22 C21 C33 F33 -10.3(12) . . . . ?
C26 C21 C33 C34 23.8(14) . . . . ?
C22 C21 C33 C34 -157.7(9) . . . . ?
C26 C21 C33 C35 -45.9(13) . . . . ?
C22 C21 C33 C35 132.6(10) . . . . ?
F33 C33 C34 F34 -4.9(11) . . . . ?
C21 C33 C34 F34 143.1(8) . . . . ?
C35 C33 C34 F34 -107.7(9) . . . . ?
F33 C33 C34 C35 102.9(9) . . . . ?
C21 C33 C34 C35 -109.2(9) . . . . ?
F34 C34 C35 F35 -0.5(13) . . . . ?
C33 C34 C35 F35 -106.5(9) . . . . ?
F34 C34 C35 C33 106.0(9) . . . . ?
F33 C33 C35 F35 3.3(11) . . . . ?
C21 C33 C35 F35 -140.6(8) . . . . ?
C34 C33 C35 F35 107.8(9) . . . . ?
F33 C33 C35 C34 -104.5(8) . . . . ?
C21 C33 C35 C34 111.6(10) . . . . ?
C46 C41 C42 C43 1.0(15) . . . . ?
C53 C41 C42 C43 -178.0(10) . . . . ?
C41 C42 C43 C44 1.4(16) . . . . ?
C42 C43 C44 C45 -2.1(14) . . . . ?
C42 C43 C44 C47 178.1(9) . . . . ?
C43 C44 C45 C46 0.3(15) . . . . ?
C47 C44 C45 C46 -179.9(10) . . . . ?
C44 C45 C46 C41 2.1(17) . . . . ?
C42 C41 C46 C45 -2.8(16) . . . . ?
C53 C41 C46 C45 176.3(10) . . . . ?
C45 C44 C47 C52 9.7(14) . . . . ?
C43 C44 C47 C52 -170.6(10) . . . . ?
C45 C44 C47 C48 -169.4(10) . . . . ?
C43 C44 C47 C48 10.4(13) . . . . ?
C52 C47 C48 C49 3.1(14) . . . . ?
C44 C47 C48 C49 -177.8(8) . . . . ?
C47 C48 C49 C50 -1.1(15) . . . . ?
C48 C49 C50 C51 -1.3(16) . . . . ?
C49 C50 C51 C52 1.5(16) . . . . ?
C50 C51 C52 C47 0.8(17) . . . . ?
C48 C47 C52 C51 -3.0(15) . . . . ?
C44 C47 C52 C51 177.9(9) . . . . ?
C42 C41 C53 F53 -23.4(14) . . . . ?
C46 C41 C53 F53 157.6(10) . . . . ?
C42 C41 C53 C54 -168.1(11) . . . . ?
C46 C41 C53 C54 12.9(17) . . . . ?
C42 C41 C53 C55 119.0(12) . . . . ?
C46 C41 C53 C55 -60.0(15) . . . . ?
F53 C53 C54 F54 -4.7(14) . . . . ?
C55 C53 C54 F54 -109.4(12) . . . . ?
C41 C53 C54 F54 140.1(11) . . . . ?
F53 C53 C54 C55 104.7(11) . . . . ?
C41 C53 C54 C55 -110.6(13) . . . . ?
F54 C54 C55 F55 -1.4(15) . . . . ?
C53 C54 C55 F55 -106.5(12) . . . . ?
F54 C54 C55 C53 105.1(11) . . . . ?
F53 C53 C55 F55 3.5(14) . . . . ?
C54 C53 C55 F55 106.4(11) . . . . ?
C41 C53 C55 F55 -138.7(10) . . . . ?
F53 C53 C55 C54 -103.0(10) . . . . ?
C41 C53 C55 C54 114.9(12) . . . . ?
C66 C61 C62 C63 0.1(15) . . . . ?
C73 C61 C62 C63 177.6(9) . . . . ?
C61 C62 C63 C64 -0.1(14) . . . . ?
C62 C63 C64 C65 0.8(14) . . . . ?
C62 C63 C64 C67 -179.8(9) . . . . ?
C63 C64 C65 C66 -1.5(15) . . . . ?
C67 C64 C65 C66 179.1(9) . . . . ?
C64 C65 C66 C61 1.5(16) . . . . ?
C62 C61 C66 C65 -0.7(15) . . . . ?
C73 C61 C66 C65 -178.2(10) . . . . ?
C63 C64 C67 C68 20.0(13) . . . . ?
C65 C64 C67 C68 -160.6(9) . . . . ?
C63 C64 C67 C72 -159.0(9) . . . . ?
C65 C64 C67 C72 20.4(14) . . . . ?
C72 C67 C68 C69 -1.3(14) . . . . ?
C64 C67 C68 C69 179.7(8) . . . . ?
C67 C68 C69 C70 -0.6(15) . . . . ?
C68 C69 C70 C71 1.3(15) . . . . ?
C69 C70 C71 C72 -0.1(15) . . . . ?
C70 C71 C72 C67 -1.9(15) . . . . ?
C68 C67 C72 C71 2.6(14) . . . . ?
C64 C67 C72 C71 -178.4(9) . . . . ?
C66 C61 C73 F73 -171.1(9) . . . . ?
C62 C61 C73 F73 11.4(14) . . . . ?
C66 C61 C73 C74 44.4(15) . . . . ?
C62 C61 C73 C74 -133.1(11) . . . . ?
C66 C61 C73 C75 -25.4(15) . . . . ?
C62 C61 C73 C75 157.1(9) . . . . ?
F73 C73 C74 F74 -4.5(13) . . . . ?
C61 C73 C74 F74 140.5(10) . . . . ?
C75 C73 C74 F74 -108.1(11) . . . . ?
F73 C73 C74 C75 103.6(10) . . . . ?
C61 C73 C74 C75 -111.4(11) . . . . ?
F74 C74 C75 F75 2.2(15) . . . . ?
C73 C74 C75 F75 -104.9(10) . . . . ?
F74 C74 C75 C73 107.0(11) . . . . ?
F73 C73 C75 F75 6.2(12) . . . . ?
C61 C73 C75 F75 -139.9(10) . . . . ?
C74 C73 C75 F75 109.4(11) . . . . ?
F73 C73 C75 C74 -103.3(10) . . . . ?
C61 C73 C75 C74 110.7(11) . . . . ?
C86 C81 C82 C83 1.8(14) . . . . ?
C93 C81 C82 C83 178.4(9) . . . . ?
C81 C82 C83 C84 -2.7(15) . . . . ?
C82 C83 C84 C85 2.4(14) . . . . ?
C82 C83 C84 C87 -177.3(9) . . . . ?
C83 C84 C85 C86 -1.4(15) . . . . ?
C87 C84 C85 C86 178.3(9) . . . . ?
C84 C85 C86 C81 0.6(16) . . . . ?
C82 C81 C86 C85 -0.8(15) . . . . ?
C93 C81 C86 C85 -177.3(10) . . . . ?
C83 C84 C87 C92 172.6(10) . . . . ?
C85 C84 C87 C92 -7.1(14) . . . . ?
C83 C84 C87 C88 -7.6(14) . . . . ?
C85 C84 C87 C88 172.7(10) . . . . ?
C92 C87 C88 C89 -2.5(15) . . . . ?
C84 C87 C88 C89 177.8(9) . . . . ?
C87 C88 C89 C90 1.8(18) . . . . ?
C88 C89 C90 C91 1.1(17) . . . . ?
C89 C90 C91 C92 -3.3(18) . . . . ?
C90 C91 C92 C87 2.7(19) . . . . ?
C88 C87 C92 C91 0.2(16) . . . . ?
C84 C87 C92 C91 179.9(10) . . . . ?
C82 C81 C93 F93 19.2(13) . . . . ?
C86 C81 C93 F93 -164.4(9) . . . . ?
C82 C81 C93 C95 166.1(9) . . . . ?
C86 C81 C93 C95 -17.5(15) . . . . ?
C82 C81 C93 C94 -124.7(11) . . . . ?
C86 C81 C93 C94 51.7(14) . . . . ?
F93 C93 C94 F94 -4.7(13) . . . . ?
C81 C93 C94 F94 139.5(10) . . . . ?
C95 C93 C94 F94 -109.0(11) . . . . ?
F93 C93 C94 C95 104.4(10) . . . . ?
C81 C93 C94 C95 -111.5(11) . . . . ?
F94 C94 C95 F95 -0.6(15) . . . . ?
C93 C94 C95 F95 -105.7(11) . . . . ?
F94 C94 C95 C93 105.1(11) . . . . ?
F93 C93 C95 F95 4.8(13) . . . . ?
C81 C93 C95 F95 -142.2(10) . . . . ?
C94 C93 C95 F95 108.5(11) . . . . ?
F93 C93 C95 C94 -103.8(10) . . . . ?
C81 C93 C95 C94 109.2(11) . . . . ?
C106 C101 C102 C103 1.4(14) . . . . ?
C113 C101 C102 C103 -175.7(9) . . . . ?
C101 C102 C103 C104 0.0(15) . . . . ?
C102 C103 C104 C105 -1.1(15) . . . . ?
C102 C103 C104 C107 -179.5(9) . . . . ?
C103 C104 C105 C106 0.9(15) . . . . ?
C107 C104 C105 C106 179.4(9) . . . . ?
C104 C105 C106 C101 0.4(16) . . . . ?
C102 C101 C106 C105 -1.6(15) . . . . ?
C113 C101 C106 C105 175.4(9) . . . . ?
C103 C104 C107 C108 -21.0(14) . . . . ?
C105 C104 C107 C108 160.6(9) . . . . ?
C103 C104 C107 C112 160.0(10) . . . . ?
C105 C104 C107 C112 -18.3(14) . . . . ?
C112 C107 C108 C109 -0.3(14) . . . . ?
C104 C107 C108 C109 -179.3(9) . . . . ?
C107 C108 C109 C110 0.3(15) . . . . ?
C108 C109 C110 C111 0.1(15) . . . . ?
C109 C110 C111 C112 -0.4(15) . . . . ?
C110 C111 C112 C107 0.4(15) . . . . ?
C108 C107 C112 C111 -0.1(14) . . . . ?
C104 C107 C112 C111 178.9(9) . . . . ?
C106 C101 C113 F113 171.5(9) . . . . ?
C102 C101 C113 F113 -11.5(12) . . . . ?
C106 C101 C113 C115 27.4(14) . . . . ?
C102 C101 C113 C115 -155.6(9) . . . . ?
C106 C101 C113 C114 -43.3(14) . . . . ?
C102 C101 C113 C114 133.7(10) . . . . ?
F113 C113 C114 F114 4.4(12) . . . . ?
C115 C113 C114 F114 107.7(10) . . . . ?
C101 C113 C114 F114 -140.6(9) . . . . ?
F113 C113 C114 C115 -103.4(9) . . . . ?
C101 C113 C114 C115 111.6(11) . . . . ?
F114 C114 C115 F115 2.1(13) . . . . ?
C113 C114 C115 F115 107.0(9) . . . . ?
F114 C114 C115 C113 -104.9(9) . . . . ?
F113 C113 C115 F115 -4.3(12) . . . . ?
C101 C113 C115 F115 140.0(9) . . . . ?
C114 C113 C115 F115 -109.3(10) . . . . ?
F113 C113 C115 C114 105.0(9) . . . . ?
C101 C113 C115 C114 -110.7(10) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the 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_31
_database_code_depnum_ccdc_archive 'CCDC 1942891'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-24 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-24
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C15 H12 F2'
_chemical_formula_moiety         'C15 H12 F2'
_chemical_formula_weight         230.26
_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                   15.873(2)
_cell_length_b                   5.6329(5)
_cell_length_c                   25.223(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.875(11)
_cell_angle_gamma                90.0000
_cell_volume                     2243.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2546
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      67.06
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960.00
_exptl_absorpt_coefficient_mu    0.839
_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  0.591
_exptl_absorpt_correction_T_max  0.992

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            22569
_diffrn_reflns_av_unetI/netI     0.0681
_diffrn_reflns_av_R_equivalents  0.0976
_diffrn_reflns_theta_max         68.367
_diffrn_reflns_theta_min         2.799
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4069
_reflns_number_gt                2504
_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).,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.1169
_refine_ls_wR_factor_ref         0.3510
_refine_ls_wR_factor_gt          0.3267
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4069
_refine_ls_number_parameters     327
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1419P)²+5.1189P] 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         0.49
_refine_diff_density_min         -0.36
_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
F13 F 0.8380(4) 0.7181(9) 0.89766(17) 0.0981(18) Uani 1 1 d . . . . .
F14 F 0.9467(5) 0.4814(17) 0.9620(3) 0.084(3) Uani 0.545(7) 1 d . . P A 1
F15A F 0.7980(6) 0.369(2) 0.9498(4) 0.092(4) Uani 0.455(7) 1 d . . P A 2
F33 F 0.6243(3) 1.2595(7) 0.91749(15) 0.0861(15) Uani 1 1 d . . . . .
F34 F 0.6914(5) 0.9127(16) 0.9748(3) 0.077(3) Uani 0.545(7) 1 d . . P A 1
F35A F 0.5315(6) 0.9745(19) 0.9702(4) 0.083(3) Uani 0.455(7) 1 d . . P A 2
C1 C 0.8724(3) 0.5311(10) 0.8185(2) 0.0425(13) Uani 1 1 d . . . . .
C2 C 0.8315(4) 0.7100(11) 0.7885(3) 0.0546(16) Uani 1 1 d . . . . .
H2 H 0.800976 0.826901 0.805800 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8340(4) 0.7233(10) 0.7346(3) 0.0533(16) Uani 1 1 d . . . . .
H3 H 0.805792 0.850810 0.715574 0.064 Uiso 1 1 calc R U . . .
C4 C 0.8765(3) 0.5556(9) 0.7067(2) 0.0376(12) Uani 1 1 d . . . . .
C5 C 0.9169(4) 0.3733(11) 0.7376(2) 0.0549(16) Uani 1 1 d . . . . .
H5 H 0.945952 0.253302 0.720274 0.066 Uiso 1 1 calc R U . . .
C6 C 0.9161(4) 0.3614(11) 0.7919(3) 0.0562(16) Uani 1 1 d . . . . .
H6 H 0.945514 0.237119 0.811337 0.067 Uiso 1 1 calc R U . . .
C7 C 0.8782(3) 0.5660(9) 0.6484(2) 0.0427(13) Uani 1 1 d . . . . .
C8 C 0.8408(4) 0.7514(12) 0.6179(3) 0.0627(18) Uani 1 1 d . . . . .
H8 H 0.813605 0.874922 0.635353 0.075 Uiso 1 1 calc R U . . .
C9 C 0.8420(4) 0.7621(14) 0.5626(3) 0.0649(19) Uani 1 1 d . . . . .
H9 H 0.817213 0.893150 0.543113 0.078 Uiso 1 1 calc R U . . .
C10 C 0.8784(4) 0.5855(12) 0.5373(3) 0.0626(18) Uani 1 1 d . . . . .
H10 H 0.878826 0.590167 0.499717 0.075 Uiso 1 1 calc R U . . .
C11 C 0.9144(7) 0.4007(14) 0.5657(3) 0.093(3) Uani 1 1 d . . . . .
H11 H 0.938906 0.274227 0.547630 0.112 Uiso 1 1 calc R U . . .
C12 C 0.9159(6) 0.3944(12) 0.6201(3) 0.077(2) Uani 1 1 d . . . . .
H12 H 0.944036 0.266415 0.638960 0.093 Uiso 1 1 calc R U . . .
C13 C 0.8687(4) 0.5136(11) 0.8771(3) 0.0545(16) Uani 1 1 d . . . . .
C14 C 0.9306(5) 0.3855(16) 0.9142(3) 0.076(2) Uani 1 1 d . . . . .
H14A H 0.976975 0.295783 0.899061 0.091 Uiso 0.545(7) 1 calc R U P A 1
H14B H 0.975921 0.296054 0.898747 0.091 Uiso 0.455(7) 1 calc R U P A 2
H14C H 0.948168 0.460607 0.949076 0.091 Uiso 0.455(7) 1 calc R U P A 2
C15 C 0.8442(6) 0.2920(16) 0.9053(3) 0.086(3) Uani 1 1 d . . . . .
H15A H 0.807238 0.309840 0.934393 0.103 Uiso 0.545(7) 1 calc R U P A 1
H15B H 0.835032 0.145041 0.883988 0.103 Uiso 0.545(7) 1 calc R U P A 1
H15C H 0.830907 0.139741 0.885861 0.103 Uiso 0.455(7) 1 calc R U P A 2
C21 C 0.6164(3) 1.0449(9) 0.8366(2) 0.0369(12) Uani 1 1 d . . . . .
C22 C 0.6575(5) 1.2244(11) 0.8132(3) 0.0610(18) Uani 1 1 d . . . . .
H22 H 0.683828 1.346602 0.834916 0.073 Uiso 1 1 calc R U . . .
C23 C 0.6618(4) 1.2326(11) 0.7588(3) 0.0581(17) Uani 1 1 d . . . . .
H23 H 0.689730 1.362400 0.744102 0.070 Uiso 1 1 calc R U . . .
C24 C 0.6261(3) 1.0545(9) 0.7248(2) 0.0358(12) Uani 1 1 d . . . . .
C25 C 0.5853(4) 0.8740(10) 0.7492(2) 0.0509(15) Uani 1 1 d . . . . .
H25 H 0.559063 0.750472 0.727771 0.061 Uiso 1 1 calc R U . . .
C26 C 0.5816(4) 0.8676(11) 0.8035(2) 0.0535(16) Uani 1 1 d . . . . .
H26 H 0.554349 0.737545 0.818592 0.064 Uiso 1 1 calc R U . . .
C27 C 0.6308(3) 1.0639(9) 0.6662(2) 0.0383(12) Uani 1 1 d . . . . .
C28 C 0.6707(5) 1.2475(12) 0.6423(3) 0.0609(18) Uani 1 1 d . . . . .
H28 H 0.696361 1.369982 0.664235 0.073 Uiso 1 1 calc R U . . .
C29 C 0.6747(4) 1.2604(12) 0.5888(3) 0.0632(18) Uani 1 1 d . . . . .
H29 H 0.701125 1.393113 0.574198 0.076 Uiso 1 1 calc R U . . .
C30 C 0.6404(4) 1.0805(11) 0.5551(3) 0.0540(16) Uani 1 1 d . . . . .
H30 H 0.644860 1.085050 0.517860 0.065 Uiso 1 1 calc R U . . .
C31 C 0.5999(6) 0.8965(13) 0.5779(3) 0.080(2) Uani 1 1 d . . . . .
H31 H 0.574210 0.773834 0.556052 0.095 Uiso 1 1 calc R U . . .
C32 C 0.5964(5) 0.8888(11) 0.6326(3) 0.067(2) Uani 1 1 d . . . . .
H32 H 0.569280 0.757804 0.647354 0.081 Uiso 1 1 calc R U . . .
C33 C 0.6140(4) 1.0398(10) 0.8950(2) 0.0451(14) Uani 1 1 d . . . . .
C34 C 0.6524(4) 0.8436(13) 0.9293(3) 0.0603(17) Uani 1 1 d . . . . .
H34A H 0.675649 0.703312 0.911368 0.072 Uiso 0.545(7) 1 calc R U P A 1
H34B H 0.675148 0.704807 0.911373 0.072 Uiso 0.455(7) 1 calc R U P A 2
H34C H 0.684136 0.887155 0.963784 0.072 Uiso 0.455(7) 1 calc R U P A 2
C35 C 0.5596(4) 0.8776(14) 0.9237(2) 0.0631(18) Uani 1 1 d . . . . .
H35A H 0.533524 0.942434 0.954616 0.076 Uiso 0.545(7) 1 calc R U P A 1
H35B H 0.524536 0.760099 0.902208 0.076 Uiso 0.545(7) 1 calc R U P A 1
H35C H 0.523004 0.759400 0.902637 0.076 Uiso 0.455(7) 1 calc R U P A 2


#==============================================================================
_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    'Superflip (Palatinus, et al., 2007)'
_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
F13 C13 1.373(7) . ?
F14 C14 1.323(10) . ?
F15A C15 1.468(14) . ?
F33 C33 1.364(6) . ?
F34 C34 1.307(9) . ?
F35A C35 1.407(11) . ?
C1 C2 1.382(8) . ?
C1 C6 1.395(8) . ?
C1 C13 1.488(9) . ?
C2 C3 1.366(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(8) . ?
C4 C7 1.475(8) . ?
C5 C6 1.370(9) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.375(8) . ?
C7 C8 1.393(8) . ?
C8 C9 1.398(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.344(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.356(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(10) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.474(9) . ?
C13 C15 1.507(10) . ?
C14 C15 1.465(12) . ?
C14 H14A 1.0000 . ?
C14 H14B 0.9900 . ?
C14 H14C 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 H15C 1.0000 . ?
C21 C22 1.370(8) . ?
C21 C26 1.380(8) . ?
C21 C33 1.479(8) . ?
C22 C23 1.379(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.402(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.382(7) . ?
C24 C27 1.489(8) . ?
C25 C26 1.379(8) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C32 1.377(8) . ?
C27 C28 1.382(8) . ?
C28 C29 1.359(9) . ?
C28 H28 0.9500 . ?
C29 C30 1.396(9) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(9) . ?
C30 H30 0.9500 . ?
C31 C32 1.385(9) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 C35 1.493(9) . ?
C33 C34 1.494(9) . ?
C34 C35 1.477(9) . ?
C34 H34A 1.0000 . ?
C34 H34B 0.9900 . ?
C34 H34C 0.9900 . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 H35C 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
C2 C1 C6 117.6(6) . . ?
C2 C1 C13 121.9(5) . . ?
C6 C1 C13 120.4(5) . . ?
C3 C2 C1 121.8(6) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 122.0(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 115.7(6) . . ?
C3 C4 C7 122.4(5) . . ?
C5 C4 C7 121.9(5) . . ?
C6 C5 C4 122.6(6) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C5 C6 C1 120.3(6) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C12 C7 C8 115.1(6) . . ?
C12 C7 C4 122.9(5) . . ?
C8 C7 C4 122.0(5) . . ?
C7 C8 C9 122.3(6) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C10 C9 C8 119.5(6) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.8(7) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 120.7(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C7 122.6(7) . . ?
C11 C12 H12 118.7 . . ?
C7 C12 H12 118.7 . . ?
F13 C13 C14 114.2(6) . . ?
F13 C13 C1 111.7(5) . . ?
C14 C13 C1 124.8(6) . . ?
F13 C13 C15 113.5(6) . . ?
C14 C13 C15 58.9(5) . . ?
C1 C13 C15 124.2(6) . . ?
F14 C14 C15 112.1(7) . . ?
F14 C14 C13 115.6(8) . . ?
C15 C14 C13 61.7(5) . . ?
F14 C14 H14A 118.3 . . ?
C15 C14 H14A 118.3 . . ?
C13 C14 H14A 118.3 . . ?
C15 C14 H14B 117.6 . . ?
C13 C14 H14B 117.6 . . ?
C15 C14 H14C 117.6 . . ?
C13 C14 H14C 117.6 . . ?
H14B C14 H14C 114.7 . . ?
C14 C15 F15A 108.1(8) . . ?
C14 C15 C13 59.5(5) . . ?
F15A C15 C13 106.9(8) . . ?
C14 C15 H15A 117.8 . . ?
C13 C15 H15A 117.8 . . ?
C14 C15 H15B 117.8 . . ?
C13 C15 H15B 117.8 . . ?
H15A C15 H15B 115.0 . . ?
C14 C15 H15C 122.0 . . ?
F15A C15 H15C 122.0 . . ?
C13 C15 H15C 122.0 . . ?
C22 C21 C26 116.9(5) . . ?
C22 C21 C33 120.4(5) . . ?
C26 C21 C33 122.6(5) . . ?
C21 C22 C23 121.8(6) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C22 C23 C24 121.7(5) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 H23 119.1 . . ?
C25 C24 C23 115.7(5) . . ?
C25 C24 C27 122.7(5) . . ?
C23 C24 C27 121.6(5) . . ?
C26 C25 C24 122.0(5) . . ?
C26 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
C25 C26 C21 121.8(5) . . ?
C25 C26 H26 119.1 . . ?
C21 C26 H26 119.1 . . ?
C32 C27 C28 115.9(6) . . ?
C32 C27 C24 122.0(5) . . ?
C28 C27 C24 122.1(5) . . ?
C29 C28 C27 122.9(6) . . ?
C29 C28 H28 118.6 . . ?
C27 C28 H28 118.6 . . ?
C28 C29 C30 120.7(6) . . ?
C28 C29 H29 119.7 . . ?
C30 C29 H29 119.7 . . ?
C31 C30 C29 117.5(6) . . ?
C31 C30 H30 121.3 . . ?
C29 C30 H30 121.3 . . ?
C30 C31 C32 120.5(6) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C27 C32 C31 122.5(6) . . ?
C27 C32 H32 118.8 . . ?
C31 C32 H32 118.8 . . ?
F33 C33 C21 112.4(5) . . ?
F33 C33 C35 113.9(5) . . ?
C21 C33 C35 124.7(5) . . ?
F33 C33 C34 114.0(5) . . ?
C21 C33 C34 122.7(5) . . ?
C35 C33 C34 59.3(4) . . ?
F34 C34 C35 115.1(6) . . ?
F34 C34 C33 114.6(7) . . ?
C35 C34 C33 60.3(4) . . ?
F34 C34 H34A 118.0 . . ?
C35 C34 H34A 118.0 . . ?
C33 C34 H34A 118.0 . . ?
C35 C34 H34B 117.7 . . ?
C33 C34 H34B 117.7 . . ?
C35 C34 H34C 117.7 . . ?
C33 C34 H34C 117.7 . . ?
H34B C34 H34C 114.9 . . ?
F35A C35 C34 111.6(7) . . ?
F35A C35 C33 114.5(7) . . ?
C34 C35 C33 60.4(4) . . ?
C34 C35 H35A 117.7 . . ?
C33 C35 H35A 117.7 . . ?
C34 C35 H35B 117.7 . . ?
C33 C35 H35B 117.7 . . ?
H35A C35 H35B 114.9 . . ?
F35A C35 H35C 119.0 . . ?
C34 C35 H35C 119.0 . . ?
C33 C35 H35C 119.0 . . ?

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
C6 C1 C2 C3 -0.5(10) . . . . ?
C13 C1 C2 C3 -178.9(6) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C2 C3 C4 C5 -0.3(9) . . . . ?
C2 C3 C4 C7 178.9(6) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C7 C4 C5 C6 179.8(6) . . . . ?
C4 C5 C6 C1 1.6(11) . . . . ?
C2 C1 C6 C5 -0.8(9) . . . . ?
C13 C1 C6 C5 177.7(6) . . . . ?
C3 C4 C7 C12 -176.2(7) . . . . ?
C5 C4 C7 C12 2.9(9) . . . . ?
C3 C4 C7 C8 3.2(9) . . . . ?
C5 C4 C7 C8 -177.6(6) . . . . ?
C12 C7 C8 C9 -0.3(10) . . . . ?
C4 C7 C8 C9 -179.8(6) . . . . ?
C7 C8 C9 C10 1.7(11) . . . . ?
C8 C9 C10 C11 -0.8(12) . . . . ?
C9 C10 C11 C12 -1.5(14) . . . . ?
C10 C11 C12 C7 3.0(15) . . . . ?
C8 C7 C12 C11 -2.1(12) . . . . ?
C4 C7 C12 C11 177.4(8) . . . . ?
C2 C1 C13 F13 -13.7(9) . . . . ?
C6 C1 C13 F13 167.9(6) . . . . ?
C2 C1 C13 C14 -158.3(7) . . . . ?
C6 C1 C13 C14 23.2(10) . . . . ?
C2 C1 C13 C15 128.4(7) . . . . ?
C6 C1 C13 C15 -50.0(9) . . . . ?
F13 C13 C14 F14 1.3(11) . . . . ?
C1 C13 C14 F14 145.2(8) . . . . ?
C15 C13 C14 F14 -102.5(9) . . . . ?
F13 C13 C14 C15 103.8(7) . . . . ?
C1 C13 C14 C15 -112.3(8) . . . . ?
C13 C14 C15 F15A -99.4(8) . . . . ?
F14 C14 C15 C13 108.2(8) . . . . ?
F13 C13 C15 C14 -105.1(7) . . . . ?
C1 C13 C15 C14 113.3(7) . . . . ?
F13 C13 C15 F15A -3.7(9) . . . . ?
C14 C13 C15 F15A 101.4(8) . . . . ?
C1 C13 C15 F15A -145.2(7) . . . . ?
C26 C21 C22 C23 2.1(10) . . . . ?
C33 C21 C22 C23 179.2(6) . . . . ?
C21 C22 C23 C24 -1.6(11) . . . . ?
C22 C23 C24 C25 1.1(10) . . . . ?
C22 C23 C24 C27 180.0(6) . . . . ?
C23 C24 C25 C26 -1.2(9) . . . . ?
C27 C24 C25 C26 179.9(6) . . . . ?
C24 C25 C26 C21 1.8(10) . . . . ?
C22 C21 C26 C25 -2.2(9) . . . . ?
C33 C21 C26 C25 -179.2(6) . . . . ?
C25 C24 C27 C32 -1.7(9) . . . . ?
C23 C24 C27 C32 179.5(7) . . . . ?
C25 C24 C27 C28 179.0(6) . . . . ?
C23 C24 C27 C28 0.2(9) . . . . ?
C32 C27 C28 C29 1.5(11) . . . . ?
C24 C27 C28 C29 -179.2(6) . . . . ?
C27 C28 C29 C30 -2.2(12) . . . . ?
C28 C29 C30 C31 2.4(11) . . . . ?
C29 C30 C31 C32 -2.1(12) . . . . ?
C28 C27 C32 C31 -1.1(11) . . . . ?
C24 C27 C32 C31 179.6(7) . . . . ?
C30 C31 C32 C27 1.5(13) . . . . ?
C22 C21 C33 F33 24.3(8) . . . . ?
C26 C21 C33 F33 -158.7(6) . . . . ?
C22 C21 C33 C35 169.3(6) . . . . ?
C26 C21 C33 C35 -13.7(9) . . . . ?
C22 C21 C33 C34 -117.7(7) . . . . ?
C26 C21 C33 C34 59.2(8) . . . . ?
F33 C33 C34 F34 -1.5(9) . . . . ?
C21 C33 C34 F34 140.1(6) . . . . ?
C35 C33 C34 F34 -106.0(7) . . . . ?
F33 C33 C34 C35 104.5(6) . . . . ?
C21 C33 C34 C35 -113.9(6) . . . . ?
C33 C34 C35 F35A -106.7(8) . . . . ?
F34 C34 C35 C33 105.2(8) . . . . ?
F33 C33 C35 F35A -2.8(9) . . . . ?
C21 C33 C35 F35A -147.4(7) . . . . ?
C34 C33 C35 F35A 101.9(8) . . . . ?
F33 C33 C35 C34 -104.7(6) . . . . ?
C21 C33 C35 C34 110.7(7) . . . . ?


#==============================================================================
# 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: Diethyl 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_19
_database_code_depnum_ccdc_archive 'CCDC 1942269'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT082_19                  
;
PROBLEM: High R1 Value ..................................       0.22 Report
RESPONSE: Poor quality crystals.
;
_vrf_PLAT084_19                  
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.60 Report
RESPONSE:  Poor quality crystals.
;
# end Validation Reply Form
_audit_creation_date             2018-09-25
_audit_creation_method           'by CrystalStructure 4.3'


_chemical_formula_sum            'C15 H10 F4'
_chemical_formula_moiety         'C15 H10 F4'
_chemical_formula_weight         266.24
_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                   5.7483(14)
_cell_length_b                   7.9388(15)
_cell_length_c                   26.104(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 95.14(3)
_cell_angle_gamma                90.0000
_cell_volume                     1186.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1738
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      68.10
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544.00
_exptl_absorpt_coefficient_mu    1.129
_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  0.413
_exptl_absorpt_correction_T_max  0.989

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

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11269
_diffrn_reflns_av_unetI/netI     0.1010
_diffrn_reflns_av_R_equivalents  0.1299
_diffrn_reflns_theta_max         76.372
_diffrn_reflns_theta_min         3.400
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2410
_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).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.2570
_refine_ls_R_factor_gt           0.2229
_refine_ls_wR_factor_ref         0.6009
_refine_ls_wR_factor_gt          0.5760
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2410
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   2.261
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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          0.002
_refine_diff_density_max         1.11
_refine_diff_density_min         -0.69
_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 0.8175(14) 0.0670(11) 0.4442(3) 0.139(3) Uani 1 1 d . . . . .
F2 F 0.869(2) 0.3777(14) 0.4881(3) 0.209(6) Uani 1 1 d . . . . .
F3 F 0.536(2) 0.4748(11) 0.4400(4) 0.173(4) Uani 1 1 d . . . . .
F4 F 0.5856(14) 0.1563(10) 0.5238(3) 0.128(3) Uani 1 1 d . . . . .
C1 C 0.5352(13) 0.1695(9) 0.3793(3) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.6249(14) 0.2449(9) 0.3390(3) 0.067(2) Uani 1 1 d . . . . .
H2 H 0.764537 0.308478 0.345401 0.081 Uiso 1 1 calc R U . . .
C3 C 0.5254(11) 0.2346(8) 0.2895(3) 0.063(2) Uani 1 1 d . . . . .
H3 H 0.600466 0.286032 0.262588 0.075 Uiso 1 1 calc R U . . .
C4 C 0.3128(12) 0.1486(8) 0.2780(3) 0.0583(18) Uani 1 1 d . . . . .
C5 C 0.2180(12) 0.0710(10) 0.3187(3) 0.068(2) Uani 1 1 d . . . . .
H5 H 0.076248 0.010039 0.312119 0.081 Uiso 1 1 calc R U . . .
C6 C 0.3218(14) 0.0787(10) 0.3688(3) 0.069(2) Uani 1 1 d . . . . .
H6 H 0.251380 0.024049 0.395827 0.083 Uiso 1 1 calc R U . . .
C7 C 0.1919(10) 0.1450(7) 0.2250(3) 0.0556(18) Uani 1 1 d . . . . .
C8 C 0.2905(14) 0.2320(9) 0.1843(4) 0.071(2) Uani 1 1 d . . . . .
H8 H 0.432782 0.292301 0.190857 0.085 Uiso 1 1 calc R U . . .
C9 C 0.1755(17) 0.2281(9) 0.1344(4) 0.077(2) Uani 1 1 d . . . . .
H9 H 0.242694 0.285182 0.107319 0.093 Uiso 1 1 calc R U . . .
C10 C -0.0283(14) 0.1447(10) 0.1241(4) 0.075(2) Uani 1 1 d . . . . .
H10 H -0.102436 0.142125 0.090113 0.090 Uiso 1 1 calc R U . . .
C11 C -0.1289(13) 0.0626(10) 0.1638(4) 0.072(2) Uani 1 1 d . . . . .
H11 H -0.272160 0.003889 0.156599 0.087 Uiso 1 1 calc R U . . .
C12 C -0.0223(12) 0.0653(9) 0.2138(3) 0.066(2) Uani 1 1 d . . . . .
H12 H -0.096504 0.012214 0.240596 0.079 Uiso 1 1 calc R U . . .
C13 C 0.6387(15) 0.1825(9) 0.4318(4) 0.073(2) Uani 1 1 d . . . . .
C14 C 0.665(3) 0.3441(14) 0.4598(5) 0.129(5) Uani 1 1 d . . . . .
C15 C 0.513(3) 0.2146(16) 0.4795(5) 0.124(5) Uani 1 1 d . . . . .
H15 H 0.340759 0.235777 0.473544 0.149 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    '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 C13 1.394(11) . ?
F2 C14 1.352(17) . ?
F3 C14 1.353(16) . ?
F4 C15 1.282(14) . ?
C1 C2 1.351(11) . ?
C1 C6 1.428(11) . ?
C1 C13 1.448(12) . ?
C2 C3 1.367(11) . ?
C2 H2 0.9500 . ?
C3 C4 1.408(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(11) . ?
C4 C7 1.493(11) . ?
C5 C6 1.390(11) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.392(9) . ?
C7 C8 1.426(11) . ?
C8 C9 1.408(12) . ?
C8 H8 0.9500 . ?
C9 C10 1.352(12) . ?
C9 H9 0.9500 . ?
C10 C11 1.392(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(11) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.478(14) . ?
C13 C15 1.518(19) . ?
C14 C15 1.47(2) . ?
C15 H15 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
C2 C1 C6 117.1(8) . . ?
C2 C1 C13 123.5(7) . . ?
C6 C1 C13 119.4(7) . . ?
C1 C2 C3 123.5(7) . . ?
C1 C2 H2 118.3 . . ?
C3 C2 H2 118.3 . . ?
C2 C3 C4 120.8(7) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 116.6(7) . . ?
C5 C4 C7 121.4(6) . . ?
C3 C4 C7 122.0(6) . . ?
C4 C5 C6 122.5(7) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 119.5(7) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C12 C7 C8 117.8(7) . . ?
C12 C7 C4 122.2(6) . . ?
C8 C7 C4 119.9(6) . . ?
C9 C8 C7 119.6(7) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 121.4(8) . . ?
C10 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C9 C10 C11 119.5(8) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.8(7) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C11 120.7(7) . . ?
C7 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
F1 C13 C1 113.9(7) . . ?
F1 C13 C14 114.5(9) . . ?
C1 C13 C14 123.1(8) . . ?
F1 C13 C15 108.4(9) . . ?
C1 C13 C15 127.0(10) . . ?
C14 C13 C15 58.9(9) . . ?
F3 C14 F2 118.5(11) . . ?
F3 C14 C15 110.1(15) . . ?
F2 C14 C15 117.4(11) . . ?
F3 C14 C13 116.6(10) . . ?
F2 C14 C13 119.2(13) . . ?
C15 C14 C13 61.9(8) . . ?
F4 C15 C14 114.2(12) . . ?
F4 C15 C13 122.6(14) . . ?
C14 C15 C13 59.2(8) . . ?
F4 C15 H15 116.1 . . ?
C14 C15 H15 116.1 . . ?
C13 C15 H15 116.1 . . ?

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
C6 C1 C2 C3 -1.7(10) . . . . ?
C13 C1 C2 C3 -179.1(7) . . . . ?
C1 C2 C3 C4 2.9(10) . . . . ?
C2 C3 C4 C5 -2.5(9) . . . . ?
C2 C3 C4 C7 175.8(6) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C7 C4 C5 C6 -177.1(6) . . . . ?
C4 C5 C6 C1 -0.2(11) . . . . ?
C2 C1 C6 C5 0.3(10) . . . . ?
C13 C1 C6 C5 177.8(6) . . . . ?
C5 C4 C7 C12 0.6(9) . . . . ?
C3 C4 C7 C12 -177.7(6) . . . . ?
C5 C4 C7 C8 177.6(7) . . . . ?
C3 C4 C7 C8 -0.7(9) . . . . ?
C12 C7 C8 C9 -2.9(10) . . . . ?
C4 C7 C8 C9 180.0(6) . . . . ?
C7 C8 C9 C10 0.7(11) . . . . ?
C8 C9 C10 C11 0.8(12) . . . . ?
C9 C10 C11 C12 0.0(11) . . . . ?
C8 C7 C12 C11 3.8(10) . . . . ?
C4 C7 C12 C11 -179.2(6) . . . . ?
C10 C11 C12 C7 -2.4(11) . . . . ?
C2 C1 C13 F1 -84.3(9) . . . . ?
C6 C1 C13 F1 98.4(9) . . . . ?
C2 C1 C13 C14 61.8(14) . . . . ?
C6 C1 C13 C14 -115.5(12) . . . . ?
C2 C1 C13 C15 135.6(9) . . . . ?
C6 C1 C13 C15 -41.7(11) . . . . ?
F1 C13 C14 F3 162.9(13) . . . . ?
C1 C13 C14 F3 17(2) . . . . ?
C15 C13 C14 F3 -99.6(18) . . . . ?
F1 C13 C14 F2 9.9(17) . . . . ?
C1 C13 C14 F2 -136.1(11) . . . . ?
C15 C13 C14 F2 107.4(14) . . . . ?
F1 C13 C14 C15 -97.5(12) . . . . ?
C1 C13 C14 C15 116.5(12) . . . . ?
F3 C14 C15 F4 -135.0(13) . . . . ?
F2 C14 C15 F4 5(2) . . . . ?
C13 C14 C15 F4 114.8(15) . . . . ?
F3 C14 C15 C13 110.2(10) . . . . ?
F2 C14 C15 C13 -110.2(15) . . . . ?
F1 C13 C15 F4 7.4(13) . . . . ?
C1 C13 C15 F4 149.3(9) . . . . ?
C14 C13 C15 F4 -100.6(13) . . . . ?
F1 C13 C15 C14 108.0(10) . . . . ?
C1 C13 C15 C14 -110.1(10) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the 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_25
_database_code_depnum_ccdc_archive 'CCDC 1942271'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           'by CrystalStructure 4.3'

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

_chemical_formula_sum            'C15 H10 F2 O'
_chemical_formula_moiety         'C15 H10 F2 O'
_chemical_formula_weight         244.24
_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                   5.9713(5)
_cell_length_b                   7.3226(6)
_cell_length_c                   26.183(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 94.546(9)
_cell_angle_gamma                90.0000
_cell_volume                     1141.26(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2160
_cell_measurement_theta_min      6.80
_cell_measurement_theta_max      67.74
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504.00
_exptl_absorpt_coefficient_mu    0.932
_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  0.517
_exptl_absorpt_correction_T_max  0.991

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

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            11359
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_theta_max         68.472
_diffrn_reflns_theta_min         3.387
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2070
_reflns_number_gt                1552
_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          0.0868
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1993
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2070
_refine_ls_number_parameters     163
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1001P)²+0.9315P] 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         0.29
_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)
;
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
F14 F -0.0912(4) 0.2887(4) -0.02339(8) 0.0724(7) Uani 1 1 d . . . . .
F15 F 0.3057(4) 0.1269(4) -0.01743(9) 0.0835(8) Uani 1 1 d . . . . .
O13 O -0.3168(4) 0.3249(4) 0.05920(11) 0.0678(8) Uani 1 1 d . . . . .
C1 C -0.0007(5) 0.3044(4) 0.11944(12) 0.0408(7) Uani 1 1 d . . . . .
C2 C -0.1127(5) 0.2352(4) 0.15984(13) 0.0431(7) Uani 1 1 d . . . . .
H2 H -0.258461 0.184613 0.153045 0.052 Uiso 1 1 calc R U . . .
C3 C -0.0176(5) 0.2384(4) 0.20922(12) 0.0412(7) Uani 1 1 d . . . . .
H3 H -0.097277 0.187124 0.235757 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1966(5) 0.3164(4) 0.22152(12) 0.0369(7) Uani 1 1 d . . . . .
C5 C 0.3037(5) 0.3910(4) 0.18060(12) 0.0409(7) Uani 1 1 d . . . . .
H5 H 0.445482 0.448514 0.187446 0.049 Uiso 1 1 calc R U . . .
C6 C 0.2106(5) 0.3838(4) 0.13079(12) 0.0423(7) Uani 1 1 d . . . . .
H6 H 0.290316 0.433069 0.103976 0.051 Uiso 1 1 calc R U . . .
C7 C 0.3016(4) 0.3169(4) 0.27484(11) 0.0367(7) Uani 1 1 d . . . . .
C8 C 0.1949(5) 0.2405(4) 0.31544(13) 0.0446(7) Uani 1 1 d . . . . .
H8 H 0.050798 0.186812 0.308695 0.054 Uiso 1 1 calc R U . . .
C9 C 0.2925(6) 0.2408(5) 0.36493(13) 0.0487(8) Uani 1 1 d . . . . .
H9 H 0.214565 0.188309 0.391568 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5031(5) 0.3167(4) 0.37625(13) 0.0454(8) Uani 1 1 d . . . . .
H10 H 0.571174 0.315803 0.410295 0.055 Uiso 1 1 calc R U . . .
C11 C 0.6122(5) 0.3941(4) 0.33665(13) 0.0449(8) Uani 1 1 d . . . . .
H11 H 0.756264 0.447633 0.343757 0.054 Uiso 1 1 calc R U . . .
C12 C 0.5145(5) 0.3944(4) 0.28719(12) 0.0416(7) Uani 1 1 d . . . . .
H12 H 0.592770 0.448154 0.260802 0.050 Uiso 1 1 calc R U . . .
C13 C -0.1143(5) 0.2988(4) 0.06697(14) 0.0482(8) Uani 1 1 d . . . . .
C14 C 0.0162(6) 0.2566(5) 0.02283(13) 0.0495(8) Uani 1 1 d . . . . .
C15 C 0.2158(6) 0.1759(5) 0.02520(14) 0.0538(9) Uani 1 1 d . . . . .
H15 H 0.294524 0.153150 0.057538 0.065 Uiso 1 1 calc R U . . .


#==============================================================================
_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    'Superflip (Palatinus, et al., 2007)'
_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
F14 C14 1.345(4) . ?
F15 C15 1.325(4) . ?
O13 C13 1.226(4) . ?
C1 C2 1.391(4) . ?
C1 C6 1.400(4) . ?
C1 C13 1.483(5) . ?
C2 C3 1.370(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.414(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C4 C7 1.484(4) . ?
C5 C6 1.377(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.399(4) . ?
C7 C12 1.406(4) . ?
C8 C9 1.378(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.477(5) . ?
C14 C15 1.327(5) . ?
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
C2 C1 C6 118.0(3) . . ?
C2 C1 C13 118.8(3) . . ?
C6 C1 C13 123.1(3) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 C7 122.3(3) . . ?
C3 C4 C7 121.5(3) . . ?
C6 C5 C4 122.3(3) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
C8 C7 C12 116.4(3) . . ?
C8 C7 C4 122.0(3) . . ?
C12 C7 C4 121.6(3) . . ?
C9 C8 C7 122.0(3) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C9 C10 C11 118.4(3) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C12 C11 C10 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C7 121.6(3) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
O13 C13 C14 118.5(3) . . ?
O13 C13 C1 121.5(3) . . ?
C14 C13 C1 120.0(3) . . ?
C15 C14 F14 118.8(3) . . ?
C15 C14 C13 125.7(3) . . ?
F14 C14 C13 115.1(3) . . ?
F15 C15 C14 120.2(3) . . ?
F15 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.1(4) . . . . ?
C13 C1 C2 C3 -179.3(3) . . . . ?
C1 C2 C3 C4 1.6(5) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C2 C3 C4 C7 -178.9(3) . . . . ?
C3 C4 C5 C6 -2.2(4) . . . . ?
C7 C4 C5 C6 177.2(3) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
C13 C1 C6 C5 177.5(3) . . . . ?
C5 C4 C7 C8 -179.3(3) . . . . ?
C3 C4 C7 C8 0.1(4) . . . . ?
C5 C4 C7 C12 0.6(4) . . . . ?
C3 C4 C7 C12 -180.0(3) . . . . ?
C12 C7 C8 C9 0.0(4) . . . . ?
C4 C7 C8 C9 179.9(3) . . . . ?
C7 C8 C9 C10 -0.4(5) . . . . ?
C8 C9 C10 C11 0.7(5) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C7 0.0(5) . . . . ?
C8 C7 C12 C11 0.2(4) . . . . ?
C4 C7 C12 C11 -179.7(3) . . . . ?
C2 C1 C13 O13 37.1(5) . . . . ?
C6 C1 C13 O13 -139.9(3) . . . . ?
C2 C1 C13 C14 -141.4(3) . . . . ?
C6 C1 C13 C14 41.6(4) . . . . ?
O13 C13 C14 C15 -159.7(4) . . . . ?
C1 C13 C14 C15 18.8(5) . . . . ?
O13 C13 C14 F14 13.6(5) . . . . ?
C1 C13 C14 F14 -167.9(3) . . . . ?
F14 C14 C15 F15 -0.6(5) . . . . ?
C13 C14 C15 F15 172.6(3) . . . . ?


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



#===END
_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_22b
_database_code_depnum_ccdc_archive 'CCDC 1942270'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_audit_creation_date             2019-07-22
_audit_creation_method           'by CrystalStructure 4.3'

# start Validation Reply Form
_vrf_PLAT971_22b                 
;PROBLEM: Check Calcd Resid. Dens.  1.81A   From I14             8.23 eA-3  
RESPONSE: Poor quality crystals.
;

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

_chemical_formula_sum            'C15 H10 F3 I'
_chemical_formula_moiety         'C15 H10 F3 I'
_chemical_formula_weight         374.14
_chemical_melting_point          ?
_chemical_absolute_configuration unk

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
_space_group_IT_number           4
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.9337(5)
_cell_length_b                   7.5484(8)
_cell_length_c                   15.1871(13)
_cell_angle_alpha                90.0000
_cell_angle_beta                 96.119(9)
_cell_angle_gamma                90.0000
_cell_volume                     676.35(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6831
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.19
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.837
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360.00
_exptl_absorpt_coefficient_mu    2.385
_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  0.732
_exptl_absorpt_correction_T_max  0.976

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

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            13055
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_av_R_equivalents  0.1185
_diffrn_reflns_theta_max         27.967
_diffrn_reflns_theta_min         2.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2883
_reflns_number_gt                2510
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.845
_reflns_Friedel_fraction_full    1.000

#==============================================================================
# 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          0.1269
_refine_ls_R_factor_gt           0.1217
_refine_ls_wR_factor_ref         0.3104
_refine_ls_wR_factor_gt          0.3049
_refine_ls_number_restraints     150
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     172
_refine_ls_goodness_of_fit_ref   1.341
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] 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          0.002
_refine_diff_density_max         7.91
_refine_diff_density_min         -1.04
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 936 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.44(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
;
International Tables 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 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
I I -0.4742 1.8119
;
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
I14 I 0.90543(19) 0.3251(4) 0.95184(7) 0.0624(6) Uani 1 1 d . . . . .
F13 F 0.8530(18) 0.6718(16) 0.8270(10) 0.060(3) Uani 1 1 d . . . . .
F14 F 0.480(2) 0.2952(18) 0.8380(8) 0.066(3) Uani 1 1 d . . . . .
F15 F 0.600(3) 0.682(4) 0.9723(14) 0.141(12) Uani 1 1 d . . . . .
C1 C 0.526(2) 0.603(2) 0.7258(12) 0.037(3) Uani 1 1 d . . . . .
C2 C 0.623(3) 0.523(2) 0.6562(11) 0.037(3) Uani 1 1 d . . . . .
H2 H 0.763661 0.463270 0.667982 0.044 Uiso 1 1 calc R U . . .
C3 C 0.519(2) 0.5300(19) 0.5694(11) 0.032(3) Uani 1 1 d . . . . .
H3 H 0.590610 0.473561 0.524028 0.039 Uiso 1 1 calc R U . . .
C4 C 0.309(2) 0.6177(14) 0.5464(11) 0.029(2) Uani 1 1 d . . . . .
C5 C 0.213(3) 0.701(2) 0.6166(13) 0.043(3) Uani 1 1 d . . . . .
H5 H 0.073874 0.763014 0.604821 0.051 Uiso 1 1 calc R U . . .
C6 C 0.319(3) 0.694(2) 0.7033(13) 0.040(3) Uani 1 1 d . . . . .
H6 H 0.248909 0.751630 0.748863 0.048 Uiso 1 1 calc R U . . .
C7 C 0.200(2) 0.6176(14) 0.4557(10) 0.027(2) Uani 1 1 d . . . . .
C8 C 0.293(3) 0.5418(18) 0.3864(11) 0.033(3) Uani 1 1 d . . . . .
H8 H 0.434629 0.483818 0.398901 0.040 Uiso 1 1 calc R U . . .
C9 C 0.191(3) 0.5432(19) 0.2951(12) 0.037(3) Uani 1 1 d . . . . .
H9 H 0.267304 0.495057 0.248573 0.044 Uiso 1 1 calc R U . . .
C10 C -0.031(3) 0.6212(18) 0.2785(12) 0.038(3) Uani 1 1 d . . . . .
H10 H -0.110949 0.619915 0.220928 0.045 Uiso 1 1 calc R U . . .
C11 C -0.129(2) 0.7017(17) 0.3524(12) 0.036(3) Uani 1 1 d . . . . .
H11 H -0.271312 0.759837 0.342864 0.044 Uiso 1 1 calc R U . . .
C12 C -0.017(2) 0.6940(16) 0.4352(12) 0.035(3) Uani 1 1 d . . . . .
H12 H -0.089283 0.743130 0.482500 0.042 Uiso 1 1 calc R U . . .
C13 C 0.636(3) 0.589(2) 0.8161(13) 0.046(3) Uani 1 1 d . . . . .
C14 C 0.623(3) 0.426(3) 0.8732(13) 0.049(3) Uani 1 1 d . . . . .
C15 C 0.503(4) 0.590(3) 0.9002(12) 0.055(4) Uani 1 1 d . . . . .
H15 H 0.334208 0.591020 0.889709 0.065 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    '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
I14 C14 2.096(19) . ?
F13 C13 1.424(19) . ?
F14 C14 1.37(2) . ?
F15 C15 1.37(2) . ?
C1 C2 1.39(2) . ?
C1 C6 1.42(2) . ?
C1 C13 1.46(2) . ?
C2 C3 1.40(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.417(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.41(2) . ?
C4 C7 1.46(2) . ?
C5 C6 1.40(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.36(2) . ?
C7 C12 1.413(19) . ?
C8 C9 1.45(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.44(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.45(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.36(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.51(3) . ?
C13 C15 1.57(3) . ?
C14 C15 1.51(3) . ?
C15 H15 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
C2 C1 C6 116.3(16) . . ?
C2 C1 C13 120.1(15) . . ?
C6 C1 C13 123.6(16) . . ?
C1 C2 C3 121.6(14) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C2 C3 C4 122.6(14) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 115.9(14) . . ?
C5 C4 C7 122.6(13) . . ?
C3 C4 C7 121.5(13) . . ?
C6 C5 C4 121.2(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C1 122.5(16) . . ?
C5 C6 H6 118.8 . . ?
C1 C6 H6 118.8 . . ?
C8 C7 C12 115.8(15) . . ?
C8 C7 C4 123.5(12) . . ?
C12 C7 C4 120.7(13) . . ?
C7 C8 C9 124.9(13) . . ?
C7 C8 H8 117.5 . . ?
C9 C8 H8 117.5 . . ?
C10 C9 C8 116.6(15) . . ?
C10 C9 H9 121.7 . . ?
C8 C9 H9 121.7 . . ?
C9 C10 C11 118.1(16) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C12 C11 C10 120.1(14) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 124.3(15) . . ?
C11 C12 H12 117.8 . . ?
C7 C12 H12 117.8 . . ?
F13 C13 C1 112.7(15) . . ?
F13 C13 C14 113.2(15) . . ?
C1 C13 C14 123.6(15) . . ?
F13 C13 C15 115.2(15) . . ?
C1 C13 C15 123.4(15) . . ?
C14 C13 C15 58.5(13) . . ?
F14 C14 C15 114.3(16) . . ?
F14 C14 C13 115.5(15) . . ?
C15 C14 C13 62.7(14) . . ?
F14 C14 I14 112.6(14) . . ?
C15 C14 I14 120.9(13) . . ?
C13 C14 I14 122.2(12) . . ?
F15 C15 C14 117.8(18) . . ?
F15 C15 C13 117(2) . . ?
C14 C15 C13 58.7(13) . . ?
F15 C15 H15 116.9 . . ?
C14 C15 H15 116.9 . . ?
C13 C15 H15 116.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1(2) . . . . ?
C13 C1 C2 C3 178.0(15) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C2 C3 C4 C7 -177.9(13) . . . . ?
C3 C4 C5 C6 -1(2) . . . . ?
C7 C4 C5 C6 177.9(15) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C2 C1 C6 C5 1(2) . . . . ?
C13 C1 C6 C5 -178.0(16) . . . . ?
C5 C4 C7 C8 178.3(14) . . . . ?
C3 C4 C7 C8 -3.0(19) . . . . ?
C5 C4 C7 C12 -3.6(18) . . . . ?
C3 C4 C7 C12 175.1(12) . . . . ?
C12 C7 C8 C9 3(2) . . . . ?
C4 C7 C8 C9 -178.4(13) . . . . ?
C7 C8 C9 C10 -4(2) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C9 C10 C11 C12 -3(2) . . . . ?
C10 C11 C12 C7 3(2) . . . . ?
C8 C7 C12 C11 -2.8(19) . . . . ?
C4 C7 C12 C11 179.0(12) . . . . ?
C2 C1 C13 F13 64(2) . . . . ?
C6 C1 C13 F13 -117.3(17) . . . . ?
C2 C1 C13 C14 -79(2) . . . . ?
C6 C1 C13 C14 100(2) . . . . ?
C2 C1 C13 C15 -150.5(18) . . . . ?
C6 C1 C13 C15 29(3) . . . . ?
F13 C13 C14 F14 -148.1(16) . . . . ?
C1 C13 C14 F14 -6(3) . . . . ?
C15 C13 C14 F14 105.5(18) . . . . ?
F13 C13 C14 C15 106.3(17) . . . . ?
C1 C13 C14 C15 -111.6(19) . . . . ?
F13 C13 C14 I14 -5(2) . . . . ?
C1 C13 C14 I14 137.5(14) . . . . ?
C15 C13 C14 I14 -111.0(17) . . . . ?
F14 C14 C15 F15 146(2) . . . . ?
C13 C14 C15 F15 -106(3) . . . . ?
I14 C14 C15 F15 7(3) . . . . ?
F14 C14 C15 C13 -107.4(18) . . . . ?
I14 C14 C15 C13 113.0(15) . . . . ?
F13 C13 C15 F15 5(3) . . . . ?
C1 C13 C15 F15 -140(2) . . . . ?
C14 C13 C15 F15 108(2) . . . . ?
F13 C13 C15 C14 -102.8(17) . . . . ?
C1 C13 C15 C14 112.0(19) . . . . ?


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


