# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_bs47
_database_code_depnum_ccdc_archive 'CCDC 1522469'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 Bis(trifluormethyl)dimethylfluoranthen 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 F6'
_chemical_formula_weight         394.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   I2/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.028(5)
_cell_length_b                   12.352(4)
_cell_length_c                   17.520(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.455(19)
_cell_angle_gamma                90.00
_cell_volume                     3358.8(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    108(2)
_cell_measurement_reflns_used    998
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      28.2

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9493
_exptl_absorpt_correction_T_max  1.0
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      108(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19536
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.35
_reflns_number_total             4176
_reflns_number_gt                3304
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0477P)²+2.7853P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4176
_refine_ls_number_parameters     257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.11509(8) -0.09867(11) 1.05761(8) 0.0215(3) Uani 1 1 d . . .
C2 C 0.11871(9) -0.21404(11) 1.05762(8) 0.0258(3) Uani 1 1 d . . .
H2 H 0.1111 -0.2510 1.1029 0.031 Uiso 1 1 calc R . .
C3 C 0.13243(9) -0.27503(11) 0.99656(9) 0.0269(3) Uani 1 1 d . . .
H3 H 0.1363 -0.3516 1.0008 0.032 Uiso 1 1 calc R . .
C4 C 0.14073(8) -0.22232(10) 0.92702(8) 0.0227(3) Uani 1 1 d . . .
C5 C 0.15182(9) -0.27403(11) 0.85819(8) 0.0256(3) Uani 1 1 d . . .
H5 H 0.1528 -0.3508 0.8552 0.031 Uiso 1 1 calc R . .
C6 C 0.16114(8) -0.21236(11) 0.79576(8) 0.0241(3) Uani 1 1 d . . .
H6 H 0.1709 -0.2486 0.7510 0.029 Uiso 1 1 calc R . .
C7 C 0.15707(8) -0.09685(10) 0.79411(8) 0.0204(3) Uani 1 1 d . . .
C8 C 0.13858(7) -0.04532(10) 0.85889(7) 0.0179(2) Uani 1 1 d . . .
C9 C 0.13654(7) -0.10922(10) 0.92604(7) 0.0189(2) Uani 1 1 d . . .
C10 C 0.12923(7) -0.04501(10) 0.99168(7) 0.0187(2) Uani 1 1 d . . .
C11 C 0.12964(7) 0.06938(10) 0.96446(7) 0.0177(2) Uani 1 1 d . . .
C12 C 0.12609(7) 0.06801(10) 0.88213(7) 0.0173(2) Uani 1 1 d . . .
C13 C 0.10925(8) 0.16275(10) 0.83700(7) 0.0185(2) Uani 1 1 d . . .
C14 C 0.11046(8) 0.26165(10) 0.87786(8) 0.0194(2) Uani 1 1 d . . .
C15 C 0.11757(8) 0.26376(10) 0.95932(8) 0.0199(2) Uani 1 1 d . . .
C16 C 0.13179(8) 0.16784(10) 1.00459(7) 0.0193(2) Uani 1 1 d . . .
C17 C 0.11307(9) 0.36443(11) 0.83096(8) 0.0244(3) Uani 1 1 d . . .
C18 C 0.10039(9) 0.36772(11) 0.99978(8) 0.0256(3) Uani 1 1 d . . .
C19 C 0.15955(9) 0.17269(11) 1.09350(8) 0.0242(3) Uani 1 1 d . . .
H19A H 0.1085 0.1726 1.1148 0.036 Uiso 1 1 calc R . .
H19B H 0.1927 0.2391 1.1099 0.036 Uiso 1 1 calc R . .
H19C H 0.1954 0.1096 1.1135 0.036 Uiso 1 1 calc R . .
C20 C 0.09114(9) -0.04831(12) 1.12755(8) 0.0260(3) Uani 1 1 d . . .
H20A H 0.1435 -0.0249 1.1660 0.039 Uiso 1 1 calc R . .
H20B H 0.0606 -0.1017 1.1520 0.039 Uiso 1 1 calc R . .
H20C H 0.0537 0.0143 1.1101 0.039 Uiso 1 1 calc R . .
C21 C 0.17822(9) -0.04337(11) 0.72380(8) 0.0255(3) Uani 1 1 d . . .
H21A H 0.1249 -0.0306 0.6830 0.038 Uiso 1 1 calc R . .
H21B H 0.2163 -0.0906 0.7028 0.038 Uiso 1 1 calc R . .
H21C H 0.2072 0.0258 0.7399 0.038 Uiso 1 1 calc R . .
C22 C 0.07753(9) 0.15828(10) 0.74807(8) 0.0230(3) Uani 1 1 d . . .
H22A H 0.0355 0.2163 0.7300 0.035 Uiso 1 1 calc R . .
H22B H 0.0502 0.0880 0.7323 0.035 Uiso 1 1 calc R . .
H22C H 0.1263 0.1676 0.7244 0.035 Uiso 1 1 calc R . .
F1 F 0.06384(6) 0.34796(7) 1.05957(5) 0.0311(2) Uani 1 1 d . . .
F2 F 0.17109(6) 0.42672(7) 1.03066(5) 0.0344(2) Uani 1 1 d . . .
F3 F 0.04424(6) 0.43240(7) 0.95057(5) 0.0336(2) Uani 1 1 d . . .
F4 F 0.15542(6) 0.44550(6) 0.87516(5) 0.0310(2) Uani 1 1 d . . .
F5 F 0.03571(6) 0.40291(7) 0.79301(5) 0.0353(2) Uani 1 1 d . . .
F6 F 0.15677(6) 0.34868(6) 0.77525(5) 0.0300(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C10 1.3985(18) . ?
C1 C2 1.4263(19) . ?
C1 C20 1.5069(19) . ?
C2 C3 1.370(2) . ?
C3 C4 1.4166(19) . ?
C4 C9 1.3985(18) . ?
C4 C5 1.415(2) . ?
C5 C6 1.371(2) . ?
C6 C7 1.4283(18) . ?
C7 C8 1.3960(18) . ?
C7 C21 1.5092(18) . ?
C8 C9 1.4239(17) . ?
C8 C12 1.4853(17) . ?
C9 C10 1.4257(18) . ?
C10 C11 1.4918(17) . ?
C11 C16 1.4008(18) . ?
C11 C12 1.4293(18) . ?
C12 C13 1.4004(17) . ?
C13 C14 1.4135(17) . ?
C13 C22 1.5144(18) . ?
C14 C15 1.4032(19) . ?
C14 C17 1.5185(18) . ?
C15 C16 1.4123(18) . ?
C15 C18 1.5247(18) . ?
C16 C19 1.5107(18) . ?
C17 F5 1.3394(16) . ?
C17 F4 1.3419(16) . ?
C17 F6 1.3500(16) . ?
C18 F2 1.3424(16) . ?
C18 F3 1.3431(17) . ?
C18 F1 1.3440(16) . ?

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
C10 C1 C2 117.31(12) . . ?
C10 C1 C20 127.06(12) . . ?
C2 C1 C20 115.53(12) . . ?
C3 C2 C1 124.30(13) . . ?
C2 C3 C4 119.12(13) . . ?
C9 C4 C5 117.16(12) . . ?
C9 C4 C3 117.08(12) . . ?
C5 C4 C3 125.76(13) . . ?
C6 C5 C4 119.41(12) . . ?
C5 C6 C7 123.88(13) . . ?
C8 C7 C6 117.19(12) . . ?
C8 C7 C21 126.91(12) . . ?
C6 C7 C21 115.81(12) . . ?
C7 C8 C9 118.18(11) . . ?
C7 C8 C12 136.31(11) . . ?
C9 C8 C12 105.27(11) . . ?
C4 C9 C8 123.57(12) . . ?
C4 C9 C10 124.00(12) . . ?
C8 C9 C10 112.42(11) . . ?
C1 C10 C9 117.73(12) . . ?
C1 C10 C11 136.68(12) . . ?
C9 C10 C11 105.15(10) . . ?
C16 C11 C12 120.44(11) . . ?
C16 C11 C10 131.56(11) . . ?
C12 C11 C10 108.00(10) . . ?
C13 C12 C11 120.89(11) . . ?
C13 C12 C8 130.77(12) . . ?
C11 C12 C8 108.29(10) . . ?
C12 C13 C14 117.38(12) . . ?
C12 C13 C22 121.21(11) . . ?
C14 C13 C22 120.75(11) . . ?
C15 C14 C13 121.23(11) . . ?
C15 C14 C17 121.91(11) . . ?
C13 C14 C17 116.57(11) . . ?
C14 C15 C16 121.08(11) . . ?
C14 C15 C18 120.68(11) . . ?
C16 C15 C18 117.91(12) . . ?
C11 C16 C15 117.79(11) . . ?
C11 C16 C19 121.06(11) . . ?
C15 C16 C19 120.70(11) . . ?
F5 C17 F4 107.09(11) . . ?
F5 C17 F6 105.98(11) . . ?
F4 C17 F6 104.22(11) . . ?
F5 C17 C14 114.73(11) . . ?
F4 C17 C14 112.95(11) . . ?
F6 C17 C14 111.11(11) . . ?
F2 C18 F3 107.38(11) . . ?
F2 C18 F1 105.83(11) . . ?
F3 C18 F1 104.82(11) . . ?
F2 C18 C15 114.35(11) . . ?
F3 C18 C15 111.87(11) . . ?
F1 C18 C15 111.96(11) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        28.35
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_fluorenthane1
_database_code_depnum_ccdc_archive 'CCDC 1522473'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
_chemical_formula_moiety         'C24 H14 F12'

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

_chemical_formula_sum            'C24 H14 F12'
_chemical_formula_weight         530.36
_chemical_melting_point          ?
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless

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

_diffrn_ambient_temperature      153

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_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                   11.817(3)
_cell_length_b                   21.237(4)
_cell_length_c                   8.2580(16)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.474(2)
_cell_angle_gamma                90.0000
_cell_volume                     2054.9(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5314
_cell_measurement_theta_min      3.14
_cell_measurement_theta_max      27.49
_cell_measurement_temperature    153
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.714
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1064.00
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  0.991
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            7879
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.850
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

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

_refine_special_details          
;
    Refinement was performed using reflections with F² > 0.1 sigma(F²).
    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).
;
_reflns_number_total             4015
_reflns_number_gt                3100
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.0599
_refine_ls_number_restraints     ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     339
_refine_ls_goodness_of_fit_ref   3.246
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     'w = 1/σ²(Fo²)'
_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         0.358
_refine_diff_density_min         -0.324
_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 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.22762(9) 0.20982(7) 0.77928(15) 0.0515(5) Uani 1.0 4 d . . .
F2 F 0.19751(10) 0.17292(7) 0.53474(17) 0.0569(5) Uani 1.0 4 d . . .
F3 F 0.21574(10) 0.11004(7) 0.73961(17) 0.0603(5) Uani 1.0 4 d . . .
F4 F -0.07207(11) -0.01550(6) 0.86121(16) 0.0560(5) Uani 1.0 4 d . . .
F5 F -0.09130(11) -0.01933(6) 0.60060(15) 0.0489(5) Uani 1.0 4 d . . .
F6 F -0.22462(11) -0.05387(7) 0.72844(19) 0.0659(5) Uani 1.0 4 d . . .
F7 F -0.60607(10) 0.34405(7) 0.75254(15) 0.0508(5) Uani 1.0 4 d . . .
F8 F -0.58537(10) 0.40453(6) 0.55144(15) 0.0524(5) Uani 1.0 4 d . . .
F9 F -0.51233(11) 0.42900(7) 0.79755(15) 0.0534(5) Uani 1.0 4 d . . .
F10 F -0.39236(11) 0.47404(6) 0.59923(15) 0.0509(5) Uani 1.0 4 d . . .
F11 F -0.29832(11) 0.47508(6) 0.84177(15) 0.0552(5) Uani 1.0 4 d . . .
F12 F -0.21161(11) 0.46636(6) 0.62909(15) 0.0518(5) Uani 1.0 4 d . . .
C1 C -0.18669(15) 0.16881(10) 0.6979(3) 0.0244(7) Uani 1.0 4 d . . .
C2 C -0.12960(16) 0.22708(10) 0.6913(3) 0.0232(6) Uani 1.0 4 d . . .
C3 C -0.01445(16) 0.22750(11) 0.6718(3) 0.0277(7) Uani 1.0 4 d . . .
C4 C 0.04401(16) 0.16820(11) 0.6934(3) 0.0279(7) Uani 1.0 4 d . . .
C5 C -0.01025(16) 0.11261(11) 0.7159(3) 0.0304(7) Uani 1.0 4 d . . .
C6 C -0.12999(17) 0.11091(10) 0.7130(3) 0.0256(7) Uani 1.0 4 d . . .
C7 C -0.19981(17) 0.05665(11) 0.7194(3) 0.0281(7) Uani 1.0 4 d . . .
C8 C -0.31488(17) 0.06386(10) 0.7142(3) 0.0320(7) Uani 1.0 4 d . . .
C9 C -0.37261(16) 0.12287(10) 0.7007(3) 0.0264(7) Uani 1.0 4 d . . .
C10 C -0.30711(16) 0.17622(10) 0.6840(3) 0.0234(6) Uani 1.0 4 d . . .
C11 C -0.32749(15) 0.24523(10) 0.6693(2) 0.0225(6) Uani 1.0 4 d . . .
C12 C -0.42856(16) 0.28075(10) 0.6448(3) 0.0271(7) Uani 1.0 4 d . . .
C13 C -0.42018(17) 0.34599(10) 0.6713(3) 0.0293(7) Uani 1.0 4 d . . .
C14 C -0.31404(19) 0.37642(10) 0.6979(3) 0.0292(7) Uani 1.0 4 d . . .
C15 C -0.21178(16) 0.34139(10) 0.7165(3) 0.0261(7) Uani 1.0 4 d . . .
C16 C -0.21968(16) 0.27649(10) 0.6904(3) 0.0231(6) Uani 1.0 4 d . . .
C17 C 0.04603(16) 0.28394(11) 0.6126(3) 0.0376(8) Uani 1.0 4 d . . .
C18 C 0.16984(18) 0.16478(13) 0.6871(4) 0.0425(9) Uani 1.0 4 d . . .
C19 C -0.14823(19) -0.00785(12) 0.7273(3) 0.0383(8) Uani 1.0 4 d . . .
C20 C -0.49816(15) 0.11930(11) 0.7139(3) 0.0391(8) Uani 1.0 4 d . . .
C21 C -0.54053(16) 0.25113(10) 0.5720(3) 0.0397(8) Uani 1.0 4 d . . .
C22 C -0.5299(2) 0.38130(12) 0.6906(3) 0.0405(8) Uani 1.0 4 d . . .
C23 C -0.3046(2) 0.44727(12) 0.6940(3) 0.0411(9) Uani 1.0 4 d . . .
C24 C -0.10045(17) 0.37198(10) 0.7861(3) 0.0374(8) Uani 1.0 4 d . . .
H1 H 0.0320 0.0757 0.7337 0.0362 Uiso 1.0 4 calc R . .
H2 H -0.3585 0.0277 0.7199 0.0387 Uiso 1.0 4 calc R . .
H3 H -0.0089 0.3116 0.5538 0.0447 Uiso 1.0 4 calc R . .
H4 H 0.0859 0.3059 0.7045 0.0456 Uiso 1.0 4 calc R . .
H5 H 0.0996 0.2703 0.5419 0.0457 Uiso 1.0 4 calc R . .
H6 H -0.5139 0.0832 0.7772 0.0478 Uiso 1.0 4 calc R . .
H7 H -0.5216 0.1567 0.7657 0.0479 Uiso 1.0 4 calc R . .
H8 H -0.5395 0.1159 0.6062 0.0483 Uiso 1.0 4 calc R . .
H9 H -0.5252 0.2142 0.5115 0.0469 Uiso 1.0 4 calc R . .
H10 H -0.5846 0.2397 0.6573 0.0473 Uiso 1.0 4 calc R . .
H11 H -0.5826 0.2809 0.5001 0.0472 Uiso 1.0 4 calc R . .
H12 H -0.1155 0.4065 0.8553 0.0445 Uiso 1.0 4 calc R . .
H13 H -0.0616 0.3873 0.6988 0.0445 Uiso 1.0 4 calc R . .
H14 H -0.0534 0.3415 0.8487 0.0445 Uiso 1.0 4 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'CRYSTALS (Carruthers, et al., 1999)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'


#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C18 1.351(3) yes . .
F2 C18 1.352(3) yes . .
F3 C18 1.331(3) yes . .
F4 C19 1.342(3) yes . .
F5 C19 1.338(3) yes . .
F6 C19 1.331(3) yes . .
F7 C22 1.348(3) yes . .
F8 C22 1.341(3) yes . .
F9 C22 1.342(3) yes . .
F10 C23 1.342(3) yes . .
F11 C23 1.349(3) yes . .
F12 C23 1.347(3) yes . .
C1 C2 1.414(3) yes . .
C1 C6 1.398(3) yes . .
C1 C10 1.421(3) yes . .
C2 C3 1.391(3) yes . .
C2 C16 1.494(3) yes . .
C3 C4 1.436(4) yes . .
C3 C17 1.509(4) yes . .
C4 C5 1.368(4) yes . .
C4 C18 1.496(3) yes . .
C5 C6 1.413(3) yes . .
C6 C7 1.422(3) yes . .
C7 C8 1.364(3) yes . .
C7 C19 1.497(4) yes . .
C8 C9 1.424(3) yes . .
C9 C10 1.389(3) yes . .
C9 C20 1.504(3) yes . .
C10 C11 1.488(3) yes . .
C11 C12 1.405(3) yes . .
C11 C16 1.427(3) yes . .
C12 C13 1.404(3) yes . .
C12 C21 1.517(3) yes . .
C13 C14 1.403(3) yes . .
C13 C22 1.524(4) yes . .
C14 C15 1.410(3) yes . .
C14 C23 1.509(4) yes . .
C15 C16 1.396(3) yes . .
C15 C24 1.512(3) yes . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 C1 C6 123.21(18) yes . . .
C2 C1 C10 112.19(18) yes . . .
C6 C1 C10 124.59(19) yes . . .
C1 C2 C3 119.3(2) yes . . .
C1 C2 C16 105.76(17) yes . . .
C3 C2 C16 134.6(2) yes . . .
C2 C3 C4 116.2(2) yes . . .
C2 C3 C17 123.7(2) yes . . .
C4 C3 C17 119.74(18) yes . . .
C3 C4 C5 123.18(18) yes . . .
C3 C4 C18 120.2(2) yes . . .
C5 C4 C18 116.6(2) yes . . .
C4 C5 C6 120.4(2) yes . . .
C1 C6 C5 116.51(19) yes . . .
C1 C6 C7 116.25(18) yes . . .
C5 C6 C7 127.2(2) yes . . .
C6 C7 C8 119.3(2) yes . . .
C6 C7 C19 120.54(19) yes . . .
C8 C7 C19 120.2(2) yes . . .
C7 C8 C9 124.5(2) yes . . .
C8 C9 C10 117.26(18) yes . . .
C8 C9 C20 114.64(19) yes . . .
C10 C9 C20 128.03(19) yes . . .
C1 C10 C9 117.82(19) yes . . .
C1 C10 C11 105.39(17) yes . . .
C9 C10 C11 136.49(18) yes . . .
C10 C11 C12 131.78(18) yes . . .
C10 C11 C16 108.41(16) yes . . .
C12 C11 C16 119.77(19) yes . . .
C11 C12 C13 117.77(18) yes . . .
C11 C12 C21 121.05(19) yes . . .
C13 C12 C21 120.74(18) yes . . .
C12 C13 C14 121.50(19) yes . . .
C12 C13 C22 117.27(19) yes . . .
C14 C13 C22 120.8(2) yes . . .
C13 C14 C15 120.7(2) yes . . .
C13 C14 C23 121.5(2) yes . . .
C15 C14 C23 117.6(2) yes . . .
C14 C15 C16 117.70(18) yes . . .
C14 C15 C24 120.36(19) yes . . .
C16 C15 C24 121.34(18) yes . . .
C2 C16 C11 107.34(18) yes . . .
C2 C16 C15 131.24(18) yes . . .
C11 C16 C15 121.25(18) yes . . .
F1 C18 F2 105.6(2) yes . . .
F1 C18 F3 106.27(18) yes . . .
F1 C18 C4 112.2(2) yes . . .
F2 C18 F3 106.1(2) yes . . .
F2 C18 C4 112.81(18) yes . . .
F3 C18 C4 113.3(2) yes . . .
F4 C19 F5 105.71(18) yes . . .
F4 C19 F6 106.8(2) yes . . .
F4 C19 C7 111.88(19) yes . . .
F5 C19 F6 106.4(2) yes . . .
F5 C19 C7 112.1(2) yes . . .
F6 C19 C7 113.54(19) yes . . .
F7 C22 F8 105.34(18) yes . . .
F7 C22 F9 104.30(19) yes . . .
F7 C22 C13 111.7(2) yes . . .
F8 C22 F9 107.6(2) yes . . .
F8 C22 C13 114.8(2) yes . . .
F9 C22 C13 112.31(19) yes . . .
F10 C23 F11 106.9(2) yes . . .
F10 C23 F12 104.40(18) yes . . .
F10 C23 C14 112.42(19) yes . . .
F11 C23 F12 106.05(18) yes . . .
F11 C23 C14 114.39(19) yes . . .
F12 C23 C14 112.0(2) yes . . .



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

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

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522471'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT201_shelx               
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          6 Report
RESPONSE: These carbon atoms are disordered.
;
# Added during the CSD deposition process: Tuesday 13 December 2016 11:54 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H16 F10'
_chemical_formula_weight         590.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   30.365(11)
_cell_length_b                   12.085(4)
_cell_length_c                   13.365(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4905(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    961
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      24.3

_exptl_crystal_description       platelett
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             2384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.146
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36886
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.814
_diffrn_reflns_theta_max         25.076
_diffrn_reflns_theta_full        25.076
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             4318
_reflns_number_gt                3122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.

 The disordered carbon atoms C27A to C32A and C27B to C32B 
 were erefined with isotropic ADPs.
;

_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0216P)²+12.6943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     423
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1364
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.51091(11) 0.1242(3) 0.4222(3) 0.0373(9) Uani 1 1 d . . . . .
C2 C 0.50867(11) 0.0630(3) 0.3314(3) 0.0379(9) Uani 1 1 d . . . . .
C3 C 0.54777(12) 0.0355(3) 0.2833(4) 0.0465(11) Uani 1 1 d . . . . .
C4 C 0.58784(13) 0.0569(4) 0.3383(4) 0.0625(14) Uani 1 1 d . . . . .
H4 H 0.6149 0.0352 0.3087 0.075 Uiso 1 1 calc R U . . .
C5 C 0.58925(13) 0.1061(4) 0.4294(4) 0.0615(14) Uani 1 1 d . . . . .
H5 H 0.6165 0.1136 0.4635 0.074 Uiso 1 1 calc R U . . .
C6 C 0.55038(12) 0.1459(3) 0.4731(4) 0.0481(11) Uani 1 1 d . . . . .
C7 C 0.54675(14) 0.2062(3) 0.5638(4) 0.0535(12) Uani 1 1 d . . . . .
H7 H 0.5725 0.2256 0.6002 0.064 Uiso 1 1 calc R U . . .
C8 C 0.50639(14) 0.2360(3) 0.5986(3) 0.0504(11) Uani 1 1 d . . . . .
H8 H 0.5050 0.2761 0.6597 0.060 Uiso 1 1 calc R U . . .
C9 C 0.46598(13) 0.2111(3) 0.5492(3) 0.0421(10) Uani 1 1 d . . . . .
C10 C 0.46895(11) 0.1610(3) 0.4552(3) 0.0346(9) Uani 1 1 d . . . . .
C11 C 0.43734(11) 0.1199(3) 0.3788(3) 0.0322(8) Uani 1 1 d . . . . .
C12 C 0.46058(11) 0.0516(3) 0.3089(3) 0.0314(8) Uani 1 1 d . . . . .
C13 C 0.43767(11) -0.0168(3) 0.2425(3) 0.0298(8) Uani 1 1 d . . . . .
C14 C 0.39149(11) -0.0060(3) 0.2396(3) 0.0302(8) Uani 1 1 d . . . . .
C15 C 0.36962(11) 0.0731(3) 0.2968(3) 0.0335(8) Uani 1 1 d . . . . .
C16 C 0.39204(11) 0.1400(3) 0.3662(3) 0.0352(8) Uani 1 1 d . . . . .
C17 C 0.55298(14) -0.0065(4) 0.1786(4) 0.0623(13) Uani 1 1 d . . . . .
H17A H 0.5546 -0.0875 0.1794 0.093 Uiso 1 1 calc R U . . .
H17B H 0.5801 0.0235 0.1496 0.093 Uiso 1 1 calc R U . . .
H17C H 0.5277 0.0170 0.1383 0.093 Uiso 1 1 calc R U . . .
C18 C 0.42460(13) 0.2344(3) 0.6066(3) 0.0542(12) Uani 1 1 d . . . . .
H18A H 0.4140 0.3087 0.5901 0.081 Uiso 1 1 calc R U . . .
H18B H 0.4307 0.2299 0.6785 0.081 Uiso 1 1 calc R U . . .
H18C H 0.4021 0.1797 0.5888 0.081 Uiso 1 1 calc R U . . .
C19 C 0.45902(12) -0.1088(3) 0.1830(3) 0.0399(9) Uani 1 1 d . . . . .
H19A H 0.4634 -0.0844 0.1138 0.060 Uiso 1 1 calc R U . . .
H19B H 0.4400 -0.1742 0.1838 0.060 Uiso 1 1 calc R U . . .
H19C H 0.4876 -0.1273 0.2128 0.060 Uiso 1 1 calc R U . . .
C20 C 0.36777(12) 0.2347(3) 0.4154(3) 0.0526(12) Uani 1 1 d . . . . .
H20A H 0.3519 0.2074 0.4743 0.079 Uiso 1 1 calc R U . . .
H20B H 0.3467 0.2666 0.3678 0.079 Uiso 1 1 calc R U . . .
H20C H 0.3889 0.2916 0.4359 0.079 Uiso 1 1 calc R U . . .
C21 C 0.36507(11) -0.0816(3) 0.1742(3) 0.0311(8) Uani 1 1 d . . . . .
C22 C 0.33834(12) -0.1634(3) 0.2152(3) 0.0414(9) Uani 1 1 d . . . . .
C23 C 0.31383(12) -0.2350(3) 0.1569(4) 0.0504(12) Uani 1 1 d . . . . .
C24 C 0.31531(13) -0.2252(4) 0.0554(4) 0.0617(14) Uani 1 1 d . . . . .
C25 C 0.34155(15) -0.1448(4) 0.0116(3) 0.0613(13) Uani 1 1 d . . . . .
C26 C 0.36594(12) -0.0759(3) 0.0722(3) 0.0433(10) Uani 1 1 d . . . . .
C27A C 0.3214(2) 0.0943(6) 0.2764(6) 0.0207(18) Uiso 0.483(6) 1 d . U P A 1
C28A C 0.2930(2) 0.0744(7) 0.3543(6) 0.0295(18) Uiso 0.483(6) 1 d . . P A 1
C29A C 0.2474(3) 0.0808(7) 0.3469(6) 0.0376(19) Uiso 0.483(6) 1 d . . P A 1
C30A C 0.2302(3) 0.1072(7) 0.2557(6) 0.038(2) Uiso 0.483(6) 1 d . . P A 1
C31A C 0.2569(2) 0.1314(6) 0.1733(6) 0.0302(18) Uiso 0.483(6) 1 d . . P A 1
C32A C 0.3017(3) 0.1241(8) 0.1860(8) 0.0201(19) Uiso 0.483(6) 1 d . . P A 1
C27B C 0.3194(2) 0.0671(7) 0.3030(6) 0.028(2) Uiso 0.517(6) 1 d . U P A 2
C28B C 0.2955(2) 0.0310(7) 0.3843(7) 0.0282(17) Uiso 0.517(6) 1 d . . P A 2
C29B C 0.2501(2) 0.0220(6) 0.3828(5) 0.0346(17) Uiso 0.517(6) 1 d . . P A 2
C30B C 0.2275(2) 0.0519(6) 0.2970(6) 0.0346(18) Uiso 0.517(6) 1 d . . P A 2
C31B C 0.2497(3) 0.0906(6) 0.2144(6) 0.0369(18) Uiso 0.517(6) 1 d . . P A 2
C32B C 0.2956(3) 0.0970(7) 0.2198(7) 0.032(2) Uiso 0.517(6) 1 d . . P A 2
F1 F 0.33623(9) -0.1739(2) 0.3147(2) 0.0734(8) Uani 1 1 d . . . . .
F2 F 0.28951(8) -0.3153(2) 0.1997(2) 0.0781(9) Uani 1 1 d . . . . .
F3 F 0.29181(9) -0.2942(3) -0.0015(3) 0.1030(13) Uani 1 1 d . . . . .
F4 F 0.34359(11) -0.1343(3) -0.0877(2) 0.1108(14) Uani 1 1 d . . . . .
F5 F 0.39128(8) 0.0010(2) 0.02666(17) 0.0597(7) Uani 1 1 d . . . . .
F6A F 0.3086(3) 0.0421(7) 0.4440(6) 0.0433(17) Uani 0.483(6) 1 d . . P A 1
F7A F 0.22113(17) 0.0631(7) 0.4239(5) 0.0651(19) Uani 0.483(6) 1 d . . P A 1
F8A F 0.18569(15) 0.1168(6) 0.2425(5) 0.064(2) Uani 0.483(6) 1 d . . P A 1
F9A F 0.23949(18) 0.1617(5) 0.0852(5) 0.0498(16) Uani 0.483(6) 1 d . . P A 1
F10A F 0.3279(3) 0.1476(10) 0.1063(8) 0.0335(18) Uani 0.483(6) 1 d . . P A 1
F6B F 0.3164(2) 0.0004(6) 0.4687(6) 0.0415(16) Uani 0.517(6) 1 d . . P A 2
F7B F 0.22808(14) -0.0159(5) 0.4643(4) 0.0538(16) Uani 0.517(6) 1 d . . P A 2
F8B F 0.18327(14) 0.0401(5) 0.2950(5) 0.0581(17) Uani 0.517(6) 1 d . . P A 2
F9B F 0.2275(2) 0.1177(5) 0.1324(5) 0.0558(16) Uani 0.517(6) 1 d . . P A 2
F10B F 0.3161(3) 0.1360(9) 0.1372(7) 0.0383(19) Uani 0.517(6) 1 d . . P A 2


_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
C1 C6 1.403(5) . ?
C1 C10 1.420(5) . ?
C1 C2 1.423(5) . ?
C2 C3 1.390(5) . ?
C2 C12 1.497(5) . ?
C3 C4 1.444(6) . ?
C3 C17 1.498(6) . ?
C4 C5 1.355(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.419(6) . ?
C7 C8 1.359(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.426(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.397(5) . ?
C9 C18 1.499(6) . ?
C10 C11 1.487(5) . ?
C11 C16 1.407(5) . ?
C11 C12 1.432(5) . ?
C12 C13 1.399(5) . ?
C13 C14 1.409(5) . ?
C13 C19 1.513(5) . ?
C14 C15 1.393(5) . ?
C14 C21 1.497(5) . ?
C15 C16 1.407(5) . ?
C15 C27A 1.512(8) . ?
C15 C27B 1.529(8) . ?
C16 C20 1.512(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.366(5) . ?
C21 C22 1.391(5) . ?
C22 F1 1.338(5) . ?
C22 C23 1.381(5) . ?
C23 F2 1.347(4) . ?
C23 C24 1.363(7) . ?
C24 F3 1.336(4) . ?
C24 C25 1.387(6) . ?
C25 F4 1.333(5) . ?
C25 C26 1.378(5) . ?
C26 F5 1.351(4) . ?
C27A C28A 1.372(11) . ?
C27A C32A 1.396(13) . ?
C28A F6A 1.347(10) . ?
C28A C29A 1.392(11) . ?
C29A F7A 1.319(9) . ?
C29A C30A 1.364(11) . ?
C30A F8A 1.367(9) . ?
C30A C31A 1.399(12) . ?
C31A F9A 1.342(10) . ?
C31A C32A 1.373(12) . ?
C32A F10A 1.360(12) . ?
C27B C32B 1.374(11) . ?
C27B C28B 1.378(12) . ?
C28B F6B 1.346(11) . ?
C28B C29B 1.382(10) . ?
C29B F7B 1.357(9) . ?
C29B C30B 1.385(10) . ?
C30B F8B 1.350(8) . ?
C30B C31B 1.377(11) . ?
C31B F9B 1.328(9) . ?
C31B C32B 1.398(11) . ?
C32B F10B 1.351(10) . ?

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 C10 123.9(4) . . ?
C6 C1 C2 123.5(4) . . ?
C10 C1 C2 112.7(3) . . ?
C3 C2 C1 118.5(3) . . ?
C3 C2 C12 135.9(4) . . ?
C1 C2 C12 105.4(3) . . ?
C2 C3 C4 116.2(4) . . ?
C2 C3 C17 127.1(4) . . ?
C4 C3 C17 116.5(4) . . ?
C5 C4 C3 124.2(4) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C6 C1 116.9(4) . . ?
C5 C6 C7 126.7(4) . . ?
C1 C6 C7 116.3(4) . . ?
C8 C7 C6 119.9(4) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C9 124.1(4) . . ?
C7 C8 H8 117.9 . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 116.9(4) . . ?
C10 C9 C18 126.6(3) . . ?
C8 C9 C18 116.4(4) . . ?
C9 C10 C1 118.2(3) . . ?
C9 C10 C11 136.1(3) . . ?
C1 C10 C11 105.1(3) . . ?
C16 C11 C12 120.2(3) . . ?
C16 C11 C10 131.0(3) . . ?
C12 C11 C10 108.8(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 C2 131.8(3) . . ?
C11 C12 C2 107.3(3) . . ?
C12 C13 C14 117.3(3) . . ?
C12 C13 C19 123.7(3) . . ?
C14 C13 C19 118.7(3) . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 C21 118.9(3) . . ?
C13 C14 C21 119.5(3) . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 C27A 118.7(4) . . ?
C16 C15 C27A 119.4(4) . . ?
C14 C15 C27B 118.2(4) . . ?
C16 C15 C27B 118.3(4) . . ?
C15 C16 C11 116.9(3) . . ?
C15 C16 C20 119.1(3) . . ?
C11 C16 C20 123.7(3) . . ?
C3 C17 H17A 109.5 . . ?
C3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C13 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 116.1(3) . . ?
C26 C21 C14 122.8(3) . . ?
C22 C21 C14 121.1(3) . . ?
F1 C22 C23 118.4(4) . . ?
F1 C22 C21 119.1(3) . . ?
C23 C22 C21 122.5(4) . . ?
F2 C23 C24 120.2(4) . . ?
F2 C23 C22 120.5(4) . . ?
C24 C23 C22 119.3(4) . . ?
F3 C24 C23 119.7(4) . . ?
F3 C24 C25 120.3(5) . . ?
C23 C24 C25 120.0(4) . . ?
F4 C25 C26 120.1(4) . . ?
F4 C25 C24 120.9(4) . . ?
C26 C25 C24 119.0(4) . . ?
F5 C26 C21 119.7(3) . . ?
F5 C26 C25 117.2(4) . . ?
C21 C26 C25 123.1(4) . . ?
C28A C27A C32A 115.6(8) . . ?
C28A C27A C15 116.2(7) . . ?
C32A C27A C15 128.0(7) . . ?
F6A C28A C27A 120.4(7) . . ?
F6A C28A C29A 115.4(8) . . ?
C27A C28A C29A 124.2(8) . . ?
F7A C29A C30A 120.3(8) . . ?
F7A C29A C28A 122.5(8) . . ?
C30A C29A C28A 117.2(8) . . ?
C29A C30A F8A 120.9(8) . . ?
C29A C30A C31A 122.0(8) . . ?
F8A C30A C31A 117.0(7) . . ?
F9A C31A C32A 121.0(8) . . ?
F9A C31A C30A 121.3(7) . . ?
C32A C31A C30A 117.7(8) . . ?
F10A C32A C31A 118.1(11) . . ?
F10A C32A C27A 118.7(10) . . ?
C31A C32A C27A 123.2(10) . . ?
C32B C27B C28B 116.4(8) . . ?
C32B C27B C15 117.8(7) . . ?
C28B C27B C15 125.8(7) . . ?
F6B C28B C27B 119.9(7) . . ?
F6B C28B C29B 117.5(8) . . ?
C27B C28B C29B 122.6(8) . . ?
F7B C29B C28B 120.4(7) . . ?
F7B C29B C30B 120.5(6) . . ?
C28B C29B C30B 119.1(7) . . ?
F8B C30B C31B 120.5(7) . . ?
F8B C30B C29B 118.9(7) . . ?
C31B C30B C29B 120.6(7) . . ?
F9B C31B C30B 119.8(8) . . ?
F9B C31B C32B 122.4(8) . . ?
C30B C31B C32B 117.8(8) . . ?
F10B C32B C27B 120.8(9) . . ?
F10B C32B C31B 115.7(9) . . ?
C27B C32B C31B 123.4(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -8.8(5) . . . . ?
C10 C1 C2 C3 171.0(3) . . . . ?
C6 C1 C2 C12 175.2(3) . . . . ?
C10 C1 C2 C12 -5.0(4) . . . . ?
C1 C2 C3 C4 9.3(5) . . . . ?
C12 C2 C3 C4 -176.2(4) . . . . ?
C1 C2 C3 C17 -166.1(4) . . . . ?
C12 C2 C3 C17 8.3(7) . . . . ?
C2 C3 C4 C5 -3.4(6) . . . . ?
C17 C3 C4 C5 172.6(4) . . . . ?
C3 C4 C5 C6 -4.1(7) . . . . ?
C4 C5 C6 C1 5.0(6) . . . . ?
C4 C5 C6 C7 -175.0(4) . . . . ?
C10 C1 C6 C5 -178.5(3) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C10 C1 C6 C7 1.5(5) . . . . ?
C2 C1 C6 C7 -178.7(3) . . . . ?
C5 C6 C7 C8 -177.7(4) . . . . ?
C1 C6 C7 C8 2.3(5) . . . . ?
C6 C7 C8 C9 -0.2(6) . . . . ?
C7 C8 C9 C10 -5.6(6) . . . . ?
C7 C8 C9 C18 170.4(4) . . . . ?
C8 C9 C10 C1 8.9(5) . . . . ?
C18 C9 C10 C1 -166.6(3) . . . . ?
C8 C9 C10 C11 179.1(4) . . . . ?
C18 C9 C10 C11 3.6(6) . . . . ?
C6 C1 C10 C9 -7.4(5) . . . . ?
C2 C1 C10 C9 172.8(3) . . . . ?
C6 C1 C10 C11 179.6(3) . . . . ?
C2 C1 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C16 16.2(7) . . . . ?
C1 C10 C11 C16 -172.7(4) . . . . ?
C9 C10 C11 C12 -165.5(4) . . . . ?
C1 C10 C11 C12 5.6(4) . . . . ?
C16 C11 C12 C13 -15.5(5) . . . . ?
C10 C11 C12 C13 166.0(3) . . . . ?
C16 C11 C12 C2 169.9(3) . . . . ?
C10 C11 C12 C2 -8.6(4) . . . . ?
C3 C2 C12 C13 19.6(7) . . . . ?
C1 C2 C12 C13 -165.5(4) . . . . ?
C3 C2 C12 C11 -166.7(4) . . . . ?
C1 C2 C12 C11 8.3(4) . . . . ?
C11 C12 C13 C14 7.2(5) . . . . ?
C2 C12 C13 C14 -179.8(3) . . . . ?
C11 C12 C13 C19 -166.0(3) . . . . ?
C2 C12 C13 C19 7.0(6) . . . . ?
C12 C13 C14 C15 3.0(5) . . . . ?
C19 C13 C14 C15 176.6(3) . . . . ?
C12 C13 C14 C21 -176.5(3) . . . . ?
C19 C13 C14 C21 -3.0(5) . . . . ?
C13 C14 C15 C16 -5.3(6) . . . . ?
C21 C14 C15 C16 174.3(3) . . . . ?
C13 C14 C15 C27A 169.0(5) . . . . ?
C21 C14 C15 C27A -11.4(6) . . . . ?
C13 C14 C15 C27B -169.9(5) . . . . ?
C21 C14 C15 C27B 9.7(6) . . . . ?
C14 C15 C16 C11 -2.8(5) . . . . ?
C27A C15 C16 C11 -177.1(5) . . . . ?
C27B C15 C16 C11 161.8(5) . . . . ?
C14 C15 C16 C20 171.6(4) . . . . ?
C27A C15 C16 C20 -2.7(6) . . . . ?
C27B C15 C16 C20 -23.8(6) . . . . ?
C12 C11 C16 C15 12.9(5) . . . . ?
C10 C11 C16 C15 -168.9(3) . . . . ?
C12 C11 C16 C20 -161.2(4) . . . . ?
C10 C11 C16 C20 16.9(6) . . . . ?
C15 C14 C21 C26 110.7(4) . . . . ?
C13 C14 C21 C26 -69.7(5) . . . . ?
C15 C14 C21 C22 -70.0(5) . . . . ?
C13 C14 C21 C22 109.6(4) . . . . ?
C26 C21 C22 F1 179.6(3) . . . . ?
C14 C21 C22 F1 0.2(5) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
C14 C21 C22 C23 -179.5(3) . . . . ?
F1 C22 C23 F2 -1.9(5) . . . . ?
C21 C22 C23 F2 177.8(3) . . . . ?
F1 C22 C23 C24 179.6(4) . . . . ?
C21 C22 C23 C24 -0.6(6) . . . . ?
F2 C23 C24 F3 1.4(6) . . . . ?
C22 C23 C24 F3 179.8(4) . . . . ?
F2 C23 C24 C25 -177.8(4) . . . . ?
C22 C23 C24 C25 0.6(7) . . . . ?
F3 C24 C25 F4 0.5(7) . . . . ?
C23 C24 C25 F4 179.7(5) . . . . ?
F3 C24 C25 C26 -179.0(4) . . . . ?
C23 C24 C25 C26 0.2(7) . . . . ?
C22 C21 C26 F5 -179.7(3) . . . . ?
C14 C21 C26 F5 -0.3(6) . . . . ?
C22 C21 C26 C25 1.0(6) . . . . ?
C14 C21 C26 C25 -179.7(4) . . . . ?
F4 C25 C26 F5 0.1(7) . . . . ?
C24 C25 C26 F5 179.6(4) . . . . ?
F4 C25 C26 C21 179.5(4) . . . . ?
C24 C25 C26 C21 -1.0(7) . . . . ?
C14 C15 C27A C28A 119.1(6) . . . . ?
C16 C15 C27A C28A -66.4(8) . . . . ?
C14 C15 C27A C32A -55.9(9) . . . . ?
C16 C15 C27A C32A 118.6(8) . . . . ?
C32A C27A C28A F6A 178.2(8) . . . . ?
C15 C27A C28A F6A 2.5(11) . . . . ?
C32A C27A C28A C29A 0.9(12) . . . . ?
C15 C27A C28A C29A -174.7(7) . . . . ?
F6A C28A C29A F7A 3.9(12) . . . . ?
C27A C28A C29A F7A -178.7(8) . . . . ?
F6A C28A C29A C30A -176.4(8) . . . . ?
C27A C28A C29A C30A 0.9(13) . . . . ?
F7A C29A C30A F8A 0.6(13) . . . . ?
C28A C29A C30A F8A -179.1(7) . . . . ?
F7A C29A C30A C31A 177.1(7) . . . . ?
C28A C29A C30A C31A -2.5(12) . . . . ?
C29A C30A C31A F9A -177.1(7) . . . . ?
F8A C30A C31A F9A -0.5(12) . . . . ?
C29A C30A C31A C32A 2.2(12) . . . . ?
F8A C30A C31A C32A 178.8(7) . . . . ?
F9A C31A C32A F10A -0.6(15) . . . . ?
C30A C31A C32A F10A -179.9(10) . . . . ?
F9A C31A C32A C27A 179.2(7) . . . . ?
C30A C31A C32A C27A -0.1(12) . . . . ?
C28A C27A C32A F10A 178.4(10) . . . . ?
C15 C27A C32A F10A -6.5(15) . . . . ?
C28A C27A C32A C31A -1.3(12) . . . . ?
C15 C27A C32A C31A 173.7(7) . . . . ?
C14 C15 C27B C32B -72.6(8) . . . . ?
C16 C15 C27B C32B 122.3(6) . . . . ?
C14 C15 C27B C28B 105.5(7) . . . . ?
C16 C15 C27B C28B -59.7(9) . . . . ?
C32B C27B C28B F6B -179.9(7) . . . . ?
C15 C27B C28B F6B 2.1(11) . . . . ?
C32B C27B C28B C29B 1.7(11) . . . . ?
C15 C27B C28B C29B -176.3(6) . . . . ?
F6B C28B C29B F7B 0.4(11) . . . . ?
C27B C28B C29B F7B 178.8(7) . . . . ?
F6B C28B C29B C30B -179.5(7) . . . . ?
C27B C28B C29B C30B -1.1(12) . . . . ?
F7B C29B C30B F8B -1.6(10) . . . . ?
C28B C29B C30B F8B 178.2(6) . . . . ?
F7B C29B C30B C31B 179.8(7) . . . . ?
C28B C29B C30B C31B -0.3(11) . . . . ?
F8B C30B C31B F9B 0.7(11) . . . . ?
C29B C30B C31B F9B 179.2(7) . . . . ?
F8B C30B C31B C32B -177.6(6) . . . . ?
C29B C30B C31B C32B 0.9(11) . . . . ?
C28B C27B C32B F10B 178.4(8) . . . . ?
C15 C27B C32B F10B -3.4(12) . . . . ?
C28B C27B C32B C31B -1.1(11) . . . . ?
C15 C27B C32B C31B 177.1(6) . . . . ?
F9B C31B C32B F10B 2.0(12) . . . . ?
C30B C31B C32B F10B -179.7(8) . . . . ?
F9B C31B C32B C27B -178.5(7) . . . . ?
C30B C31B C32B C27B -0.2(12) . . . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_bs127a
_database_code_depnum_ccdc_archive 'CCDC 1522467'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT041_bs127a              
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: The disordered H-atoms at C17 and C19 are not included in the refinement.  That causes differences in the unit cell content and the atom list.
;
# Added during the CSD deposition process: Tuesday 13 December 2016 11:54 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 F9'
_chemical_formula_weight         462.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.943(2)
_cell_length_b                   9.827(2)
_cell_length_c                   21.451(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.064(5)
_cell_angle_gamma                90.00
_cell_volume                     1870.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    955
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      30.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936
_exptl_absorpt_coefficient_mu    0.158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.806
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-AXS SMART CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14069
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         26.37
_reflns_number_total             3819
_reflns_number_gt                3395
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 The disordered H-atoms at C17 and C19 are not included in the refinement.
 That causes differences in the unit cell content and the atom list.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0203P)²+2.5087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3819
_refine_ls_number_parameters     330
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.2375(2) 0.6159(2) -0.05694(11) 0.0228(5) Uani 1 1 d . . .
C3 C 0.2845(2) 0.1998(2) 0.15226(10) 0.0203(4) Uani 1 1 d . . .
C4 C 0.0874(2) 0.7679(2) -0.00108(11) 0.0243(5) Uani 1 1 d . . .
H4 H 0.0301 0.8493 -0.0011 0.029 Uiso 1 1 calc R . .
C5 C 0.3061(2) 0.3978(2) -0.00118(10) 0.0186(4) Uani 1 1 d . . .
C6 C 0.1835(2) 0.5663(2) 0.05219(10) 0.0184(4) Uani 1 1 d . . .
C7 C 0.2208(2) 0.4417(2) 0.16077(10) 0.0195(4) Uani 1 1 d . . .
C8 C 0.2962(2) 0.2130(2) 0.08757(10) 0.0193(4) Uani 1 1 d . . .
C9 C 0.2237(2) 0.4520(2) 0.09610(10) 0.0178(4) Uani 1 1 d . . .
C10 C 0.2420(2) 0.5303(2) -0.00434(10) 0.0197(4) Uani 1 1 d . . .
C11 C 0.2439(2) 0.3114(2) 0.18783(10) 0.0200(4) Uani 1 1 d . . .
C12 C 0.3295(3) 0.0639(2) 0.18327(11) 0.0257(5) Uani 1 1 d . . .
C13 C 0.2108(3) 0.2953(2) 0.25534(11) 0.0254(5) Uani 1 1 d . . .
C14 C 0.0948(2) 0.6821(2) 0.05289(11) 0.0209(4) Uani 1 1 d . . .
C15 C 0.3876(2) 0.3567(2) -0.04909(10) 0.0219(5) Uani 1 1 d . . .
C16 C 0.3872(3) 0.4461(3) -0.10143(11) 0.0253(5) Uani 1 1 d . . .
H16 H 0.4413 0.4186 -0.1347 0.030 Uiso 1 1 calc R . .
C17 C 0.3143(3) 0.5689(3) -0.10701(11) 0.0272(5) Uani 1 1 d . . .
C18 C 0.4813(3) 0.2303(2) -0.05023(11) 0.0271(5) Uani 1 1 d . . .
H18A H 0.5230 0.2063 -0.0073 0.041 Uiso 1 1 calc R . .
H18B H 0.5637 0.2465 -0.0755 0.041 Uiso 1 1 calc R . .
H18C H 0.4182 0.1555 -0.0687 0.041 Uiso 1 1 calc R . .
C19 C 0.1578(3) 0.7401(2) -0.05281(11) 0.0253(5) Uani 1 1 d . . .
C20 C 0.2788(2) 0.3438(2) 0.06139(10) 0.0182(4) Uani 1 1 d . . .
C21 C 0.2182(3) 0.5688(2) 0.20087(11) 0.0235(5) Uani 1 1 d . . .
H21A H 0.2531 0.6468 0.1781 0.035 Uiso 1 1 calc R . .
H21B H 0.2847 0.5561 0.2403 0.035 Uiso 1 1 calc R . .
H21C H 0.1152 0.5857 0.2101 0.035 Uiso 1 1 calc R . .
C22 C -0.0001(3) 0.7201(2) 0.10336(11) 0.0247(5) Uani 1 1 d . . .
H22A H -0.0372 0.6373 0.1218 0.037 Uiso 1 1 calc R . .
H22B H -0.0858 0.7753 0.0851 0.037 Uiso 1 1 calc R . .
H22C H 0.0607 0.7725 0.1361 0.037 Uiso 1 1 calc R . .
C23 C 0.3032(3) 0.0899(2) 0.04560(11) 0.0243(5) Uani 1 1 d . . .
H23A H 0.2620 0.1135 0.0025 0.036 Uiso 1 1 calc R . .
H23B H 0.2439 0.0157 0.0608 0.036 Uiso 1 1 calc R . .
H23C H 0.4082 0.0608 0.0464 0.036 Uiso 1 1 calc R . .
C40 C 0.1556(3) 0.8378(3) -0.10644(13) 0.0230(6) Uani 0.798(3) 1 d P . .
C41 C 0.3040(13) 0.6795(16) -0.1564(5) 0.036(3) Uani 0.202(3) 1 d P . .
F1 F 0.39948(16) 0.07983(15) 0.24191(6) 0.0315(3) Uani 1 1 d . . .
F2 F 0.42941(18) -0.00289(15) 0.15298(7) 0.0368(4) Uani 1 1 d . . .
F3 F 0.21388(17) -0.02124(14) 0.18624(7) 0.0364(4) Uani 1 1 d . . .
F4 F 0.33071(17) 0.31709(16) 0.29801(6) 0.0343(3) Uani 1 1 d . . .
F5 F 0.15695(16) 0.17111(14) 0.26678(6) 0.0302(3) Uani 1 1 d . . .
F6 F 0.10309(17) 0.38175(15) 0.26908(7) 0.0342(4) Uani 1 1 d . . .
F7 F 0.2935(2) 0.8867(2) -0.11310(9) 0.0328(5) Uani 0.798(3) 1 d P . .
F8 F 0.0694(2) 0.94656(17) -0.09800(9) 0.0333(5) Uani 0.798(3) 1 d P . .
F9 F 0.1020(2) 0.78504(19) -0.16234(8) 0.0291(4) Uani 0.798(3) 1 d P . .
F10 F 0.3444(9) 0.8168(8) -0.1396(4) 0.037(2) Uani 0.202(3) 1 d P . .
F11 F 0.1632(9) 0.7048(9) -0.1903(4) 0.045(2) Uani 0.202(3) 1 d P . .
F12 F 0.3931(9) 0.6496(8) -0.1986(3) 0.040(2) Uani 0.202(3) 1 d P . .


_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
C2 C10 1.404(3) . ?
C2 C19 1.421(3) . ?
C2 C17 1.421(3) . ?
C3 C11 1.409(3) . ?
C3 C8 1.410(3) . ?
C3 C12 1.523(3) . ?
C4 C19 1.369(3) . ?
C4 C14 1.427(3) . ?
C5 C15 1.391(3) . ?
C5 C10 1.421(3) . ?
C5 C20 1.491(3) . ?
C6 C14 1.388(3) . ?
C6 C10 1.423(3) . ?
C6 C9 1.481(3) . ?
C7 C9 1.395(3) . ?
C7 C11 1.411(3) . ?
C7 C21 1.519(3) . ?
C8 C20 1.403(3) . ?
C8 C23 1.514(3) . ?
C9 C20 1.420(3) . ?
C11 C13 1.522(3) . ?
C12 F3 1.338(3) . ?
C12 F2 1.340(3) . ?
C12 F1 1.343(3) . ?
C13 F4 1.339(3) . ?
C13 F6 1.344(3) . ?
C13 F5 1.346(3) . ?
C14 C22 1.503(3) . ?
C15 C16 1.425(3) . ?
C15 C18 1.500(3) . ?
C16 C17 1.370(4) . ?
C17 C41 1.512(16) . ?
C19 C40 1.497(4) . ?
C40 F9 1.340(3) . ?
C40 F8 1.342(3) . ?
C40 F7 1.348(3) . ?
C41 F12 1.312(13) . ?
C41 F11 1.397(15) . ?
C41 F10 1.431(16) . ?
F7 F10 1.033(8) . ?
F9 F11 1.166(10) . ?

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
C10 C2 C19 115.4(2) . . ?
C10 C2 C17 116.3(2) . . ?
C19 C2 C17 128.2(2) . . ?
C11 C3 C8 121.1(2) . . ?
C11 C3 C12 121.16(19) . . ?
C8 C3 C12 117.59(19) . . ?
C19 C4 C14 124.0(2) . . ?
C15 C5 C10 118.4(2) . . ?
C15 C5 C20 136.1(2) . . ?
C10 C5 C20 105.01(18) . . ?
C14 C6 C10 118.9(2) . . ?
C14 C6 C9 135.2(2) . . ?
C10 C6 C9 105.51(18) . . ?
C9 C7 C11 117.12(19) . . ?
C9 C7 C21 120.5(2) . . ?
C11 C7 C21 121.71(19) . . ?
C20 C8 C3 117.41(19) . . ?
C20 C8 C23 120.31(19) . . ?
C3 C8 C23 121.6(2) . . ?
C7 C9 C20 121.1(2) . . ?
C7 C9 C6 130.93(19) . . ?
C20 C9 C6 107.88(18) . . ?
C2 C10 C5 124.0(2) . . ?
C2 C10 C6 123.9(2) . . ?
C5 C10 C6 112.06(19) . . ?
C3 C11 C7 121.2(2) . . ?
C3 C11 C13 121.9(2) . . ?
C7 C11 C13 116.73(19) . . ?
F3 C12 F2 106.37(19) . . ?
F3 C12 F1 107.57(18) . . ?
F2 C12 F1 104.45(18) . . ?
F3 C12 C3 113.87(19) . . ?
F2 C12 C3 111.96(19) . . ?
F1 C12 C3 112.01(19) . . ?
F4 C13 F6 106.53(19) . . ?
F4 C13 F5 107.13(18) . . ?
F6 C13 F5 104.56(18) . . ?
F4 C13 C11 113.63(19) . . ?
F6 C13 C11 111.84(19) . . ?
F5 C13 C11 112.54(19) . . ?
C6 C14 C4 116.5(2) . . ?
C6 C14 C22 125.9(2) . . ?
C4 C14 C22 117.6(2) . . ?
C5 C15 C16 116.9(2) . . ?
C5 C15 C18 126.6(2) . . ?
C16 C15 C18 116.4(2) . . ?
C17 C16 C15 124.5(2) . . ?
C16 C17 C2 119.3(2) . . ?
C16 C17 C41 133.0(5) . . ?
C2 C17 C41 107.6(5) . . ?
C4 C19 C2 120.4(2) . . ?
C4 C19 C40 122.0(2) . . ?
C2 C19 C40 117.6(2) . . ?
C8 C20 C9 120.28(19) . . ?
C8 C20 C5 131.57(19) . . ?
C9 C20 C5 108.14(18) . . ?
F9 C40 F8 106.3(2) . . ?
F9 C40 F7 105.9(2) . . ?
F8 C40 F7 106.2(2) . . ?
F9 C40 C19 114.1(2) . . ?
F8 C40 C19 111.2(2) . . ?
F7 C40 C19 112.6(2) . . ?
F12 C41 F11 105.4(10) . . ?
F12 C41 F10 103.2(9) . . ?
F11 C41 F10 98.4(11) . . ?
F12 C41 C17 109.4(11) . . ?
F11 C41 C17 117.8(8) . . ?
F10 C41 C17 120.7(8) . . ?
F10 F7 C40 107.0(5) . . ?
F11 F9 C40 125.7(4) . . ?
F7 F10 C41 130.6(8) . . ?
F9 F11 C41 107.6(8) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_bscn
_database_code_depnum_ccdc_archive 'CCDC 1522472'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H16 N2'
_chemical_formula_weight         308.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   I2/a

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.017(2)
_cell_length_b                   7.1071(14)
_cell_length_c                   35.635(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.848(5)
_cell_angle_gamma                90.00
_cell_volume                     3039.7(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    955
_cell_measurement_theta_min      3.4
_cell_measurement_theta_max      30.4

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER-AXS SMart CCD'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14214
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         30.60
_reflns_number_total             4509
_reflns_number_gt                3611
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker-AXS)'
_computing_cell_refinement       'SAINT (Bruker-AXS)'
_computing_data_reduction        'SAINT (Bruker-AXS)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0751P)²+1.2309P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4509
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1313
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.09639(8) 0.27236(14) 0.13434(3) 0.0182(2) Uani 1 1 d . . .
C2 C -0.05059(8) 0.25315(14) 0.09840(3) 0.0182(2) Uani 1 1 d . . .
C3 C -0.12342(9) 0.21351(16) 0.06783(3) 0.0216(2) Uani 1 1 d . . .
C4 C -0.23963(9) 0.21202(16) 0.07409(3) 0.0245(2) Uani 1 1 d . . .
H4 H -0.2899 0.1873 0.0533 0.029 Uiso 1 1 calc R . .
C5 C -0.28354(9) 0.24420(16) 0.10840(3) 0.0244(2) Uani 1 1 d . . .
H5 H -0.3619 0.2464 0.1107 0.029 Uiso 1 1 calc R . .
C6 C -0.21074(9) 0.27386(15) 0.14012(3) 0.0204(2) Uani 1 1 d . . .
C7 C -0.24188(9) 0.30561(16) 0.17746(3) 0.0235(2) Uani 1 1 d . . .
H7 H -0.3182 0.3029 0.1832 0.028 Uiso 1 1 calc R . .
C8 C -0.16126(9) 0.34024(15) 0.20517(3) 0.0223(2) Uani 1 1 d . . .
H8 H -0.1844 0.3667 0.2297 0.027 Uiso 1 1 calc R . .
C9 C -0.04472(8) 0.33881(14) 0.19929(3) 0.0192(2) Uani 1 1 d . . .
C10 C -0.01294(8) 0.28977(14) 0.16355(3) 0.0176(2) Uani 1 1 d . . .
C11 C 0.09379(8) 0.26463(14) 0.14536(3) 0.0176(2) Uani 1 1 d . . .
C12 C 0.07170(8) 0.26630(14) 0.10542(3) 0.0181(2) Uani 1 1 d . . .
C13 C 0.15999(9) 0.28681(15) 0.08136(3) 0.0195(2) Uani 1 1 d . . .
C14 C 0.26813(9) 0.26980(15) 0.09762(3) 0.0199(2) Uani 1 1 d . . .
C15 C 0.28781(8) 0.23160(15) 0.13606(3) 0.0191(2) Uani 1 1 d . . .
C16 C 0.20046(8) 0.22742(14) 0.16072(3) 0.0182(2) Uani 1 1 d . . .
C17 C -0.09025(10) 0.16121(19) 0.02897(3) 0.0292(3) Uani 1 1 d . . .
H17A H -0.0797 0.2758 0.0143 0.044 Uiso 1 1 calc R . .
H17B H -0.1490 0.0842 0.0166 0.044 Uiso 1 1 calc R . .
H17C H -0.0205 0.0896 0.0307 0.044 Uiso 1 1 calc R . .
C18 C 0.03125(9) 0.40569(18) 0.23138(3) 0.0259(2) Uani 1 1 d . . .
H18A H 0.0528 0.2987 0.2475 0.039 Uiso 1 1 calc R . .
H18B H -0.0076 0.4995 0.2461 0.039 Uiso 1 1 calc R . .
H18C H 0.0981 0.4624 0.2215 0.039 Uiso 1 1 calc R . .
C19 C 0.22494(9) 0.16929(16) 0.20079(3) 0.0227(2) Uani 1 1 d . . .
H19A H 0.2495 0.2791 0.2156 0.034 Uiso 1 1 calc R . .
H19B H 0.2839 0.0738 0.2018 0.034 Uiso 1 1 calc R . .
H19C H 0.1574 0.1170 0.2111 0.034 Uiso 1 1 calc R . .
C20 C 0.14589(10) 0.34048(18) 0.04053(3) 0.0262(2) Uani 1 1 d . . .
H20A H 0.2079 0.4215 0.0338 0.039 Uiso 1 1 calc R . .
H20B H 0.0754 0.4083 0.0362 0.039 Uiso 1 1 calc R . .
H20C H 0.1452 0.2266 0.0250 0.039 Uiso 1 1 calc R . .
C21 C 0.36264(9) 0.28598(16) 0.07461(3) 0.0239(2) Uani 1 1 d . . .
C22 C 0.39946(9) 0.20278(16) 0.15127(3) 0.0230(2) Uani 1 1 d . . .
N1 N 0.43872(9) 0.29723(17) 0.05636(3) 0.0336(3) Uani 1 1 d . . .
N2 N 0.48708(8) 0.18063(17) 0.16491(3) 0.0326(2) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3997(14) . ?
C1 C10 1.4143(15) . ?
C1 C2 1.4255(14) . ?
C2 C3 1.3918(15) . ?
C2 C12 1.4814(14) . ?
C3 C4 1.4252(16) . ?
C3 C17 1.5065(15) . ?
C4 C5 1.3748(16) . ?
C5 C6 1.4103(17) . ?
C6 C7 1.4181(15) . ?
C7 C8 1.3706(17) . ?
C8 C9 1.4263(14) . ?
C9 C10 1.3920(13) . ?
C9 C18 1.5044(16) . ?
C10 C11 1.4763(13) . ?
C11 C16 1.3938(15) . ?
C11 C12 1.4351(14) . ?
C12 C13 1.4043(13) . ?
C13 C14 1.4016(15) . ?
C13 C20 1.5054(15) . ?
C14 C15 1.4048(15) . ?
C14 C21 1.4379(14) . ?
C15 C16 1.4024(13) . ?
C15 C22 1.4366(15) . ?
C16 C19 1.5014(15) . ?
C21 N1 1.1507(14) . ?
C22 N2 1.1484(16) . ?

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 C10 123.81(9) . . ?
C6 C1 C2 123.96(10) . . ?
C10 C1 C2 112.23(9) . . ?
C3 C2 C1 117.83(9) . . ?
C3 C2 C12 136.45(9) . . ?
C1 C2 C12 105.45(9) . . ?
C2 C3 C4 117.51(10) . . ?
C2 C3 C17 125.78(10) . . ?
C4 C3 C17 116.62(10) . . ?
C5 C4 C3 124.08(11) . . ?
C4 C5 C6 119.18(10) . . ?
C1 C6 C5 117.09(10) . . ?
C1 C6 C7 116.49(10) . . ?
C5 C6 C7 126.42(10) . . ?
C8 C7 C6 119.63(10) . . ?
C7 C8 C9 123.85(9) . . ?
C10 C9 C8 116.88(10) . . ?
C10 C9 C18 126.22(9) . . ?
C8 C9 C18 116.70(9) . . ?
C9 C10 C1 118.59(9) . . ?
C9 C10 C11 135.71(10) . . ?
C1 C10 C11 105.43(8) . . ?
C16 C11 C12 120.81(9) . . ?
C16 C11 C10 130.74(9) . . ?
C12 C11 C10 108.21(9) . . ?
C13 C12 C11 119.89(9) . . ?
C13 C12 C2 132.59(10) . . ?
C11 C12 C2 107.45(8) . . ?
C14 C13 C12 116.86(10) . . ?
C14 C13 C20 118.61(9) . . ?
C12 C13 C20 124.34(10) . . ?
C13 C14 C15 121.83(9) . . ?
C13 C14 C21 119.98(10) . . ?
C15 C14 C21 118.16(10) . . ?
C16 C15 C14 121.34(10) . . ?
C16 C15 C22 118.34(10) . . ?
C14 C15 C22 120.28(9) . . ?
C11 C16 C15 116.89(9) . . ?
C11 C16 C19 123.95(9) . . ?
C15 C16 C19 118.97(9) . . ?
N1 C21 C14 179.29(15) . . ?
N2 C22 C15 177.13(12) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        30.60
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         0.420
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.062
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522470'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H28 F24'
_chemical_formula_weight         1060.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.479(2)
_cell_length_b                   11.3269(19)
_cell_length_c                   29.181(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.941(2)
_cell_angle_gamma                90
_cell_volume                     4035.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5135
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      26.6

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.746
_exptl_crystal_F_000             2128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.179
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9319
_exptl_absorpt_correction_T_max  0.9483
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25789
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         3.006
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             8738
_reflns_number_gt                7359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0788P)²+2.5627P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8738
_refine_ls_number_parameters     657
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1453
_refine_ls_wR_factor_gt          0.1387
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.90604(14) 0.97205(16) 0.55567(6) 0.0218(4) Uani 1 1 d . . . . .
C2 C 1.16526(16) 1.14213(17) 0.61287(7) 0.0284(4) Uani 1 1 d . . . . .
H2A H 1.1547 1.1904 0.6394 0.043 Uiso 1 1 calc R U . . .
H2B H 1.1601 1.1923 0.5851 0.043 Uiso 1 1 calc R U . . .
H2C H 1.2376 1.1048 0.6203 0.043 Uiso 1 1 calc R U . . .
C3 C 0.84575(15) 0.75921(17) 0.56286(7) 0.0257(4) Uani 1 1 d . . . . .
H3A H 0.8450 0.7211 0.5326 0.039 Uiso 1 1 calc R U . . .
H3B H 0.7736 0.7936 0.5627 0.039 Uiso 1 1 calc R U . . .
H3C H 0.8631 0.7005 0.5880 0.039 Uiso 1 1 calc R U . . .
C4 C 1.24606(15) 0.55929(16) 0.66494(6) 0.0209(3) Uani 1 1 d . . . . .
C5 C 1.08497(14) 0.60823(15) 0.60222(6) 0.0210(3) Uani 1 1 d . . . . .
C6 C 0.47544(16) 0.43112(19) 0.57882(7) 0.0282(4) Uani 1 1 d . . . . .
C7 C 0.93121(14) 0.85530(16) 0.57095(6) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.85351(16) 0.44762(18) 0.65524(7) 0.0309(4) Uani 1 1 d . . . . .
H8A H 0.8396 0.3920 0.6791 0.046 Uiso 1 1 calc R U . . .
H8B H 0.9323 0.4506 0.6559 0.046 Uiso 1 1 calc R U . . .
H8C H 0.8145 0.4215 0.6242 0.046 Uiso 1 1 calc R U . . .
C9 C 0.57064(15) 0.45088(17) 0.61338(7) 0.0259(4) Uani 1 1 d . . . . .
C10 C 1.10081(14) 0.93226(15) 0.61908(6) 0.0191(3) Uani 1 1 d . . . . .
C11 C 1.03444(14) 0.83584(15) 0.59955(6) 0.0190(3) Uani 1 1 d . . . . .
C12 C 0.41291(16) 0.5276(2) 0.55602(7) 0.0294(4) Uani 1 1 d . . . . .
C13 C 0.77590(16) 0.81955(17) 0.67408(7) 0.0263(4) Uani 1 1 d . . . . .
C14 C 0.97590(15) 1.06719(16) 0.57249(6) 0.0219(3) Uani 1 1 d . . . . .
C15 C 1.19298(14) 0.88543(15) 0.65469(6) 0.0194(3) Uani 1 1 d . . . . .
C16 C 1.16015(15) 0.52851(16) 0.62928(6) 0.0229(4) Uani 1 1 d . . . . .
H16 H 1.1503 0.4469 0.6222 0.028 Uiso 1 1 calc R U . . .
C17 C 0.30105(17) 0.5081(2) 0.52365(7) 0.0338(5) Uani 1 1 d . . . . .
C18 C 1.19059(14) 0.76013(15) 0.64963(6) 0.0195(3) Uani 1 1 d . . . . .
C19 C 1.30489(16) 0.45565(16) 0.69150(6) 0.0242(4) Uani 1 1 d . . . . .
C20 C 0.87127(15) 0.76343(18) 0.70070(6) 0.0267(4) Uani 1 1 d . . . . .
C21 C 0.54216(15) 0.66410(18) 0.60001(6) 0.0266(4) Uani 1 1 d . . . . .
C22 C 0.80469(16) 0.99088(19) 0.51697(7) 0.0296(4) Uani 1 1 d . . . . .
C23 C 1.46521(15) 0.68733(17) 0.73096(7) 0.0260(4) Uani 1 1 d . . . . .
C24 C 1.25685(16) 1.05668(17) 0.71217(7) 0.0290(4) Uani 1 1 d . . . . .
H24A H 1.3054 1.1102 0.6996 0.043 Uiso 1 1 calc R U . . .
H24B H 1.2791 1.0539 0.7464 0.043 Uiso 1 1 calc R U . . .
H24C H 1.1813 1.0853 0.7033 0.043 Uiso 1 1 calc R U . . .
C25 C 0.89022(15) 0.64438(18) 0.69380(7) 0.0278(4) Uani 1 1 d . . . . .
H25 H 0.9585 0.6119 0.7091 0.033 Uiso 1 1 calc R U . . .
C26 C 0.60790(15) 0.56737(17) 0.62008(6) 0.0243(4) Uani 1 1 d . . . . .
C27 C 0.59392(16) 0.77368(17) 0.62183(7) 0.0259(4) Uani 1 1 d . . . . .
C28 C 1.35725(14) 0.74118(16) 0.70682(6) 0.0223(4) Uani 1 1 d . . . . .
C29 C 0.82358(17) 1.04415(18) 0.67856(7) 0.0304(4) Uani 1 1 d . . . . .
C30 C 0.56002(17) 0.89011(18) 0.62417(7) 0.0303(4) Uani 1 1 d . . . . .
C31 C 0.39762(17) 0.7443(2) 0.53387(8) 0.0371(5) Uani 1 1 d . . . . .
H31A H 0.3740 0.7154 0.5017 0.056 Uiso 1 1 calc R U . . .
H31B H 0.4517 0.8074 0.5346 0.056 Uiso 1 1 calc R U . . .
H31C H 0.3342 0.7750 0.5450 0.056 Uiso 1 1 calc R U . . .
C32 C 1.34891(15) 0.85958(16) 0.71574(6) 0.0240(4) Uani 1 1 d . . . . .
H32 H 1.4042 0.8936 0.7393 0.029 Uiso 1 1 calc R U . . .
C33 C 0.71087(15) 0.61663(17) 0.64811(6) 0.0241(4) Uani 1 1 d . . . . .
C34 C 0.64146(18) 0.97142(18) 0.64491(8) 0.0319(4) Uani 1 1 d . . . . .
H34 H 0.6226 1.0528 0.6435 0.038 Uiso 1 1 calc R U . . .
C35 C 1.07775(15) 1.04774(15) 0.60311(6) 0.0213(3) Uani 1 1 d . . . . .
C36 C 1.26410(14) 0.93486(16) 0.69243(6) 0.0222(3) Uani 1 1 d . . . . .
C37 C 0.95387(16) 0.81802(18) 0.73972(7) 0.0289(4) Uani 1 1 d . . . . .
C38 C 1.26920(14) 0.68217(15) 0.67499(6) 0.0198(3) Uani 1 1 d . . . . .
C39 C 0.74738(17) 0.94093(18) 0.66727(7) 0.0283(4) Uani 1 1 d . . . . .
C40 C 1.00701(16) 0.55644(16) 0.56081(6) 0.0258(4) Uani 1 1 d . . . . .
H40A H 0.9380 0.5359 0.5699 0.039 Uiso 1 1 calc R U . . .
H40B H 1.0394 0.4853 0.5502 0.039 Uiso 1 1 calc R U . . .
H40C H 0.9928 0.6144 0.5353 0.039 Uiso 1 1 calc R U . . .
C41 C 0.44817(16) 0.64468(19) 0.56493(7) 0.0282(4) Uani 1 1 d . . . . .
C42 C 0.44592(17) 0.3032(2) 0.56506(7) 0.0328(4) Uani 1 1 d . . . . .
C43 C 0.62083(17) 0.35524(18) 0.64703(8) 0.0320(4) Uani 1 1 d . . . . .
H43A H 0.6713 0.3081 0.6329 0.048 Uiso 1 1 calc R U . . .
H43B H 0.5628 0.3043 0.6540 0.048 Uiso 1 1 calc R U . . .
H43C H 0.6610 0.3913 0.6761 0.048 Uiso 1 1 calc R U . . .
C44 C 0.69682(16) 0.74004(17) 0.64962(6) 0.0258(4) Uani 1 1 d . . . . .
C45 C 1.09537(14) 0.72555(15) 0.61581(6) 0.0186(3) Uani 1 1 d . . . . .
C46 C 0.94281(17) 1.19448(18) 0.56168(7) 0.0290(4) Uani 1 1 d . . . . .
C47 C 0.81388(15) 0.56852(17) 0.66529(6) 0.0256(4) Uani 1 1 d . . . . .
C48 C 0.44577(18) 0.9391(2) 0.60851(9) 0.0398(5) Uani 1 1 d . . . . .
H48A H 0.4366 0.9693 0.5765 0.060 Uiso 1 1 calc R U . . .
H48B H 0.4344 1.0033 0.6295 0.060 Uiso 1 1 calc R U . . .
H48C H 0.3921 0.8764 0.6094 0.060 Uiso 1 1 calc R U . . .
F1 F 1.49631(9) 0.59690(10) 0.70741(4) 0.0293(3) Uani 1 1 d . . . . .
F2 F 0.24892(10) 0.41446(12) 0.53722(4) 0.0376(3) Uani 1 1 d . . . . .
F3 F 1.54678(9) 0.76704(11) 0.73512(5) 0.0365(3) Uani 1 1 d . . . . .
F4 F 0.83447(10) 1.21277(11) 0.55376(5) 0.0370(3) Uani 1 1 d . . . . .
F5 F 1.23785(10) 0.36215(10) 0.69062(4) 0.0325(3) Uani 1 1 d . . . . .
F6 F 0.91893(10) 0.91569(11) 0.75775(4) 0.0343(3) Uani 1 1 d . . . . .
F7 F 0.81694(11) 1.10003(11) 0.71842(5) 0.0408(3) Uani 1 1 d . . . . .
F8 F 0.82089(11) 1.07574(12) 0.48680(4) 0.0375(3) Uani 1 1 d . . . . .
F9 F 0.98332(11) 1.26662(10) 0.59805(5) 0.0371(3) Uani 1 1 d . . . . .
F10 F 1.38911(10) 0.41550(10) 0.67359(4) 0.0312(3) Uani 1 1 d . . . . .
F11 F 0.97891(11) 0.74200(12) 0.77607(4) 0.0385(3) Uani 1 1 d . . . . .
F12 F 1.46632(10) 0.64994(11) 0.77489(4) 0.0349(3) Uani 1 1 d . . . . .
F13 F 0.53460(11) 0.23334(12) 0.57147(5) 0.0423(3) Uani 1 1 d . . . . .
F14 F 0.78024(11) 0.89453(12) 0.49002(4) 0.0404(3) Uani 1 1 d . . . . .
F15 F 0.23254(10) 0.59823(13) 0.52469(5) 0.0444(3) Uani 1 1 d . . . . .
F16 F 0.92864(9) 1.01652(11) 0.68052(4) 0.0328(3) Uani 1 1 d . . . . .
F17 F 0.97894(12) 1.23831(11) 0.52478(5) 0.0424(3) Uani 1 1 d . . . . .
F18 F 0.37747(12) 0.25421(12) 0.58948(5) 0.0456(3) Uani 1 1 d . . . . .
F19 F 1.34327(10) 0.47960(10) 0.73675(4) 0.0284(2) Uani 1 1 d . . . . .
F20 F 1.04929(10) 0.84474(12) 0.72790(5) 0.0390(3) Uani 1 1 d . . . . .
F21 F 0.79970(12) 1.12714(11) 0.64464(5) 0.0436(3) Uani 1 1 d . . . . .
F22 F 0.40016(11) 0.29265(13) 0.51939(5) 0.0413(3) Uani 1 1 d . . . . .
F23 F 0.30619(11) 0.49093(15) 0.47870(4) 0.0477(4) Uani 1 1 d . . . . .
F24 F 0.71437(10) 1.01822(13) 0.53242(5) 0.0416(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C14 1.409(3) . ?
C1 C7 1.410(3) . ?
C1 C22 1.526(2) . ?
C2 C35 1.513(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C7 1.508(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C16 1.375(2) . ?
C4 C38 1.439(2) . ?
C4 C19 1.511(2) . ?
C5 C45 1.385(2) . ?
C5 C16 1.419(2) . ?
C5 C40 1.505(2) . ?
C6 C9 1.408(3) . ?
C6 C12 1.425(3) . ?
C6 C42 1.528(3) . ?
C7 C11 1.400(2) . ?
C8 C47 1.505(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C26 1.399(3) . ?
C9 C43 1.508(3) . ?
C10 C35 1.398(2) . ?
C10 C11 1.417(2) . ?
C10 C15 1.480(2) . ?
C11 C45 1.488(2) . ?
C12 C41 1.404(3) . ?
C12 C17 1.531(3) . ?
C13 C44 1.415(3) . ?
C13 C39 1.424(3) . ?
C13 C20 1.429(3) . ?
C14 C35 1.412(2) . ?
C14 C46 1.515(3) . ?
C15 C36 1.382(2) . ?
C15 C18 1.427(2) . ?
C16 H16 0.9500 . ?
C17 F15 1.336(3) . ?
C17 F23 1.340(2) . ?
C17 F2 1.346(3) . ?
C18 C38 1.410(2) . ?
C18 C45 1.433(2) . ?
C19 F19 1.336(2) . ?
C19 F10 1.346(2) . ?
C19 F5 1.347(2) . ?
C20 C25 1.391(3) . ?
C20 C37 1.502(3) . ?
C21 C41 1.405(3) . ?
C21 C26 1.420(3) . ?
C21 C27 1.481(3) . ?
C22 F24 1.334(2) . ?
C22 F14 1.343(2) . ?
C22 F8 1.346(2) . ?
C23 F1 1.335(2) . ?
C23 F3 1.347(2) . ?
C23 F12 1.347(2) . ?
C23 C28 1.513(2) . ?
C24 C36 1.505(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C47 1.418(3) . ?
C25 H25 0.9500 . ?
C26 C33 1.482(3) . ?
C27 C30 1.391(3) . ?
C27 C44 1.422(3) . ?
C28 C32 1.374(3) . ?
C28 C38 1.447(2) . ?
C29 F16 1.338(2) . ?
C29 F7 1.342(2) . ?
C29 F21 1.353(2) . ?
C29 C39 1.500(3) . ?
C30 C34 1.412(3) . ?
C30 C48 1.510(3) . ?
C31 C41 1.502(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 C36 1.418(2) . ?
C32 H32 0.9500 . ?
C33 C47 1.391(3) . ?
C33 C44 1.411(3) . ?
C34 C39 1.391(3) . ?
C34 H34 0.9500 . ?
C37 F6 1.336(2) . ?
C37 F20 1.341(2) . ?
C37 F11 1.352(2) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C42 F18 1.341(2) . ?
C42 F13 1.342(3) . ?
C42 F22 1.342(2) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C46 F4 1.340(2) . ?
C46 F17 1.345(2) . ?
C46 F9 1.352(2) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?

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
C14 C1 C7 121.72(16) . . ?
C14 C1 C22 120.60(16) . . ?
C7 C1 C22 117.48(16) . . ?
C35 C2 H2A 109.5 . . ?
C35 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C35 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C7 C3 H3A 109.5 . . ?
C7 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C7 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C16 C4 C38 119.43(16) . . ?
C16 C4 C19 114.27(16) . . ?
C38 C4 C19 126.24(16) . . ?
C45 C5 C16 116.06(15) . . ?
C45 C5 C40 127.62(16) . . ?
C16 C5 C40 116.24(16) . . ?
C9 C6 C12 120.78(18) . . ?
C9 C6 C42 117.44(19) . . ?
C12 C6 C42 121.70(17) . . ?
C11 C7 C1 116.97(16) . . ?
C11 C7 C3 120.89(16) . . ?
C1 C7 C3 121.56(16) . . ?
C47 C8 H8A 109.5 . . ?
C47 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C47 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C26 C9 C6 117.17(18) . . ?
C26 C9 C43 120.34(17) . . ?
C6 C9 C43 121.81(18) . . ?
C35 C10 C11 121.61(15) . . ?
C35 C10 C15 130.22(16) . . ?
C11 C10 C15 108.11(15) . . ?
C7 C11 C10 120.50(16) . . ?
C7 C11 C45 131.97(16) . . ?
C10 C11 C45 107.54(14) . . ?
C41 C12 C6 121.15(18) . . ?
C41 C12 C17 117.48(19) . . ?
C6 C12 C17 121.23(19) . . ?
C44 C13 C39 114.58(18) . . ?
C44 C13 C20 113.99(17) . . ?
C39 C13 C20 131.42(18) . . ?
C1 C14 C35 120.82(16) . . ?
C1 C14 C46 122.22(16) . . ?
C35 C14 C46 116.82(16) . . ?
C36 C15 C18 118.79(16) . . ?
C36 C15 C10 133.80(16) . . ?
C18 C15 C10 106.71(14) . . ?
C4 C16 C5 125.59(17) . . ?
C4 C16 H16 117.2 . . ?
C5 C16 H16 117.2 . . ?
F15 C17 F23 107.07(18) . . ?
F15 C17 F2 104.18(16) . . ?
F23 C17 F2 107.31(18) . . ?
F15 C17 C12 112.43(18) . . ?
F23 C17 C12 113.74(17) . . ?
F2 C17 C12 111.51(18) . . ?
C38 C18 C15 124.84(16) . . ?
C38 C18 C45 125.29(16) . . ?
C15 C18 C45 109.85(15) . . ?
F19 C19 F10 107.65(15) . . ?
F19 C19 F5 105.82(15) . . ?
F10 C19 F5 105.00(14) . . ?
F19 C19 C4 112.70(14) . . ?
F10 C19 C4 113.52(15) . . ?
F5 C19 C4 111.56(15) . . ?
C25 C20 C13 120.00(17) . . ?
C25 C20 C37 113.48(17) . . ?
C13 C20 C37 126.36(18) . . ?
C41 C21 C26 120.23(19) . . ?
C41 C21 C27 131.95(19) . . ?
C26 C21 C27 107.81(16) . . ?
F24 C22 F14 106.32(17) . . ?
F24 C22 F8 107.87(16) . . ?
F14 C22 F8 104.12(16) . . ?
F24 C22 C1 114.27(16) . . ?
F14 C22 C1 111.89(16) . . ?
F8 C22 C1 111.71(17) . . ?
F1 C23 F3 105.41(15) . . ?
F1 C23 F12 107.56(15) . . ?
F3 C23 F12 105.44(15) . . ?
F1 C23 C28 113.28(15) . . ?
F3 C23 C28 110.79(15) . . ?
F12 C23 C28 113.73(16) . . ?
C36 C24 H24A 109.5 . . ?
C36 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C36 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C20 C25 C47 123.98(18) . . ?
C20 C25 H25 118.0 . . ?
C47 C25 H25 118.0 . . ?
C9 C26 C21 121.53(18) . . ?
C9 C26 C33 131.08(18) . . ?
C21 C26 C33 107.34(16) . . ?
C30 C27 C44 118.30(18) . . ?
C30 C27 C21 134.89(19) . . ?
C44 C27 C21 106.43(16) . . ?
C32 C28 C38 119.67(16) . . ?
C32 C28 C23 113.59(16) . . ?
C38 C28 C23 126.66(16) . . ?
F16 C29 F7 108.00(17) . . ?
F16 C29 F21 105.03(16) . . ?
F7 C29 F21 105.24(16) . . ?
F16 C29 C39 113.47(16) . . ?
F7 C29 C39 114.09(16) . . ?
F21 C29 C39 110.32(17) . . ?
C27 C30 C34 116.12(18) . . ?
C27 C30 C48 127.7(2) . . ?
C34 C30 C48 116.17(19) . . ?
C41 C31 H31A 109.5 . . ?
C41 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C41 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C28 C32 C36 125.05(16) . . ?
C28 C32 H32 117.5 . . ?
C36 C32 H32 117.5 . . ?
C47 C33 C44 119.25(18) . . ?
C47 C33 C26 133.05(18) . . ?
C44 C33 C26 106.92(16) . . ?
C39 C34 C30 124.68(19) . . ?
C39 C34 H34 117.7 . . ?
C30 C34 H34 117.7 . . ?
C10 C35 C14 116.94(16) . . ?
C10 C35 C2 120.51(16) . . ?
C14 C35 C2 121.96(16) . . ?
C15 C36 C32 115.53(16) . . ?
C15 C36 C24 126.65(16) . . ?
C32 C36 C24 117.75(15) . . ?
F6 C37 F20 107.09(16) . . ?
F6 C37 F11 105.05(16) . . ?
F20 C37 F11 105.80(16) . . ?
F6 C37 C20 114.24(17) . . ?
F20 C37 C20 113.85(16) . . ?
F11 C37 C20 110.10(16) . . ?
C18 C38 C4 114.21(15) . . ?
C18 C38 C28 113.63(15) . . ?
C4 C38 C28 132.15(16) . . ?
C34 C39 C13 119.41(18) . . ?
C34 C39 C29 114.02(18) . . ?
C13 C39 C29 126.38(19) . . ?
C5 C40 H40A 109.5 . . ?
C5 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C5 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C12 C41 C21 117.71(18) . . ?
C12 C41 C31 121.40(18) . . ?
C21 C41 C31 120.33(19) . . ?
F18 C42 F13 106.22(18) . . ?
F18 C42 F22 107.69(17) . . ?
F13 C42 F22 104.77(17) . . ?
F18 C42 C6 113.48(17) . . ?
F13 C42 C6 112.06(17) . . ?
F22 C42 C6 112.06(18) . . ?
C9 C43 H43A 109.5 . . ?
C9 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C9 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C33 C44 C13 124.62(18) . . ?
C33 C44 C27 110.56(17) . . ?
C13 C44 C27 124.78(18) . . ?
C5 C45 C18 118.32(15) . . ?
C5 C45 C11 134.65(16) . . ?
C18 C45 C11 106.63(14) . . ?
F4 C46 F17 107.35(16) . . ?
F4 C46 F9 104.01(16) . . ?
F17 C46 F9 105.81(17) . . ?
F4 C46 C14 113.89(17) . . ?
F17 C46 C14 113.32(16) . . ?
F9 C46 C14 111.73(15) . . ?
C33 C47 C25 115.65(18) . . ?
C33 C47 C8 127.06(18) . . ?
C25 C47 C8 117.24(17) . . ?
C30 C48 H48A 109.5 . . ?
C30 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C30 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?

_refine_diff_density_max         0.640
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.057

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1522468'
_audit_update_record             
;
2016-12-13 deposited with the CCDC.
2017-02-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 F3'
_chemical_formula_sum            'C42 H34 F6'
_chemical_formula_weight         652.69

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   21.1643(12)
_cell_length_b                   11.9365(6)
_cell_length_c                   12.8317(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.535(2)
_cell_angle_gamma                90
_cell_volume                     3107.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6103
_cell_measurement_theta_max      24.858
_cell_measurement_theta_min      2.377

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_F_000             1360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.950
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7177
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker-AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23923
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5485
_reflns_number_gt                3871
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+3.0113P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5485
_refine_ls_number_parameters     441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1301
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.55065(10) 0.42278(17) 0.10511(16) 0.0570(6) Uani 1 1 d . . . . .
F2 F 0.50822(8) 0.27819(16) 0.15723(16) 0.0546(6) Uani 1 1 d . . . . .
F3 F 0.53936(8) 0.41757(15) 0.26509(15) 0.0497(5) Uani 1 1 d . . . . .
C1 C 0.79210(12) 0.0724(2) 0.4228(2) 0.0201(6) Uani 1 1 d . . . . .
C2 C 0.72279(12) 0.0636(2) 0.3954(2) 0.0200(6) Uani 1 1 d . . . . .
C3 C 0.69534(14) -0.0350(2) 0.4215(2) 0.0296(7) Uani 1 1 d . . . . .
C4 C 0.73909(17) -0.1129(2) 0.4897(2) 0.0368(8) Uani 1 1 d . . . . .
H4 H 0.720896 -0.178301 0.512042 0.044 Uiso 1 1 calc R U . . .
C5 C 0.80506(17) -0.0988(2) 0.5243(2) 0.0382(8) Uani 1 1 d . . . . .
H5 H 0.831615 -0.151649 0.572839 0.046 Uiso 1 1 calc R U . . .
C6 C 0.83486(14) -0.0061(2) 0.4889(2) 0.0308(7) Uani 1 1 d . . . . .
C7 C 0.90273(15) 0.0181(3) 0.5129(2) 0.0413(9) Uani 1 1 d . . . . .
H7 H 0.934183 -0.031399 0.557474 0.050 Uiso 1 1 calc R U . . .
C8 C 0.92318(14) 0.1121(3) 0.4723(2) 0.0398(8) Uani 1 1 d . . . . .
H8 H 0.969255 0.125709 0.490264 0.048 Uiso 1 1 calc R U . . .
C9 C 0.88058(14) 0.1910(3) 0.4050(2) 0.0337(7) Uani 1 1 d . . . . .
C10 C 0.81302(12) 0.1685(2) 0.3768(2) 0.0210(6) Uani 1 1 d . . . . .
C11 C 0.75111(13) 0.2240(2) 0.3120(2) 0.0199(6) Uani 1 1 d . . . . .
C12 C 0.73932(14) 0.3151(2) 0.2401(2) 0.0264(6) Uani 1 1 d . . . . .
C13 C 0.67426(15) 0.3504(2) 0.1996(2) 0.0309(7) Uani 1 1 d . . . . .
H13 H 0.664627 0.409427 0.147780 0.037 Uiso 1 1 calc R U . . .
C14 C 0.62343(13) 0.3038(2) 0.2314(2) 0.0265(6) Uani 1 1 d . . . . .
C15 C 0.63336(13) 0.2116(2) 0.3021(2) 0.0257(6) Uani 1 1 d . . . . .
C16 C 0.69721(12) 0.1653(2) 0.3326(2) 0.0185(6) Uani 1 1 d . . . . .
C17 C 0.62473(15) -0.0713(3) 0.3777(3) 0.0416(8) Uani 1 1 d . . . . .
H17A H 0.599827 -0.047007 0.427445 0.062 Uiso 1 1 calc R U . . .
H17B H 0.622721 -0.153075 0.371045 0.062 Uiso 1 1 calc R U . . .
H17C H 0.605590 -0.037388 0.306088 0.062 Uiso 1 1 calc R U . . .
C18 C 0.91229(15) 0.2945(3) 0.3753(3) 0.0496(9) Uani 1 1 d . . . . .
H18A H 0.914150 0.288305 0.300089 0.074 Uiso 1 1 calc R U . . .
H18B H 0.957076 0.302004 0.424091 0.074 Uiso 1 1 calc R U . . .
H18C H 0.886303 0.360497 0.382441 0.074 Uiso 1 1 calc R U . . .
C19 C 0.58127(14) 0.1741(3) 0.3542(3) 0.0372(8) Uani 1 1 d . . . . .
H19A H 0.549694 0.125038 0.303929 0.056 Uiso 1 1 calc R U . . .
H19B H 0.558156 0.239784 0.371002 0.056 Uiso 1 1 calc R U . . .
H19C H 0.602167 0.133206 0.421366 0.056 Uiso 1 1 calc R U . . .
C20 C 0.78942(16) 0.3733(2) 0.1959(3) 0.0375(8) Uani 1 1 d . . . . .
H20A H 0.812105 0.430991 0.247380 0.056 Uiso 1 1 calc R U . . .
H20B H 0.767121 0.408201 0.126034 0.056 Uiso 1 1 calc R U . . .
H20C H 0.821619 0.318477 0.185714 0.056 Uiso 1 1 calc R U . . .
C21 C 0.55621(15) 0.3550(3) 0.1900(3) 0.0403(8) Uani 1 1 d . . . . .
F4 F 0.96880(8) 0.48250(14) 0.58286(14) 0.0387(4) Uani 1 1 d . . . . .
F5 F 0.98859(8) 0.44148(15) 0.75185(14) 0.0414(5) Uani 1 1 d . . . . .
F6 F 0.93964(8) 0.32332(13) 0.63031(14) 0.0405(4) Uani 1 1 d . . . . .
C22 C 0.72129(14) 0.7241(2) 0.7131(2) 0.0245(6) Uani 1 1 d . . . . .
C23 C 0.78969(13) 0.7171(2) 0.7557(2) 0.0249(6) Uani 1 1 d . . . . .
C24 C 0.82096(15) 0.7904(2) 0.8402(2) 0.0310(7) Uani 1 1 d . . . . .
C25 C 0.78096(18) 0.8752(2) 0.8682(3) 0.0412(8) Uani 1 1 d . . . . .
H25 H 0.801351 0.926413 0.924326 0.049 Uiso 1 1 calc R U . . .
C26 C 0.7160(2) 0.8863(3) 0.8193(3) 0.0495(9) Uani 1 1 d . . . . .
H26 H 0.692543 0.946927 0.838795 0.059 Uiso 1 1 calc R U . . .
C27 C 0.68237(17) 0.8092(3) 0.7397(3) 0.0402(8) Uani 1 1 d . . . . .
C28 C 0.61403(17) 0.8074(3) 0.6842(3) 0.0468(9) Uani 1 1 d . . . . .
H28 H 0.585448 0.863140 0.698251 0.056 Uiso 1 1 calc R U . . .
C29 C 0.59027(16) 0.7255(3) 0.6112(3) 0.0472(9) Uani 1 1 d . . . . .
H29 H 0.544500 0.727308 0.574199 0.057 Uiso 1 1 calc R U . . .
C30 C 0.62743(14) 0.6374(3) 0.5851(3) 0.0386(8) Uani 1 1 d . . . . .
C31 C 0.69420(13) 0.6349(2) 0.6403(2) 0.0264(6) Uani 1 1 d . . . . .
C32 C 0.75300(13) 0.5621(2) 0.6415(2) 0.0201(6) Uani 1 1 d . . . . .
C33 C 0.75803(13) 0.4579(2) 0.5952(2) 0.0223(6) Uani 1 1 d . . . . .
C34 C 0.82103(13) 0.4182(2) 0.6049(2) 0.0257(6) Uani 1 1 d . . . . .
H34 H 0.826053 0.345978 0.577075 0.031 Uiso 1 1 calc R U . . .
C35 C 0.87765(13) 0.4812(2) 0.6545(2) 0.0230(6) Uani 1 1 d . . . . .
C36 C 0.87361(13) 0.5854(2) 0.7004(2) 0.0227(6) Uani 1 1 d . . . . .
C37 C 0.81021(13) 0.6203(2) 0.7027(2) 0.0214(6) Uani 1 1 d . . . . .
C38 C 0.89031(15) 0.7832(3) 0.9112(2) 0.0380(8) Uani 1 1 d . . . . .
H38A H 0.905639 0.705511 0.913737 0.057 Uiso 1 1 calc R U . . .
H38B H 0.892187 0.808203 0.984729 0.057 Uiso 1 1 calc R U . . .
H38C H 0.918618 0.831204 0.881594 0.057 Uiso 1 1 calc R U . . .
C39 C 0.59048(15) 0.5586(3) 0.4972(3) 0.0543(10) Uani 1 1 d . . . . .
H39A H 0.617760 0.540747 0.449201 0.081 Uiso 1 1 calc R U . . .
H39B H 0.549469 0.594180 0.454878 0.081 Uiso 1 1 calc R U . . .
H39C H 0.580155 0.489515 0.530279 0.081 Uiso 1 1 calc R U . . .
C40 C 0.70147(15) 0.3810(2) 0.5400(2) 0.0356(7) Uani 1 1 d . . . . .
H40A H 0.682685 0.404585 0.464311 0.053 Uiso 1 1 calc R U . . .
H40B H 0.667457 0.384802 0.578143 0.053 Uiso 1 1 calc R U . . .
H40C H 0.717657 0.303912 0.541772 0.053 Uiso 1 1 calc R U . . .
C41 C 0.93289(13) 0.6607(2) 0.7344(2) 0.0297(7) Uani 1 1 d . . . . .
H41A H 0.959820 0.639462 0.807331 0.045 Uiso 1 1 calc R U . . .
H41B H 0.918444 0.738588 0.735264 0.045 Uiso 1 1 calc R U . . .
H41C H 0.959045 0.653048 0.682898 0.045 Uiso 1 1 calc R U . . .
C42 C 0.94296(14) 0.4333(2) 0.6553(2) 0.0305(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.335(4) . ?
F2 C21 1.344(4) . ?
F3 C21 1.345(3) . ?
C1 C6 1.407(4) . ?
C1 C2 1.412(4) . ?
C1 C10 1.417(4) . ?
C2 C3 1.395(4) . ?
C2 C16 1.472(4) . ?
C3 C4 1.424(4) . ?
C3 C17 1.503(4) . ?
C4 C5 1.350(5) . ?
C5 C6 1.411(4) . ?
C6 C7 1.411(4) . ?
C7 C8 1.358(5) . ?
C8 C9 1.416(4) . ?
C9 C10 1.398(4) . ?
C9 C18 1.505(4) . ?
C10 C11 1.493(4) . ?
C11 C12 1.402(4) . ?
C11 C16 1.426(4) . ?
C12 C13 1.392(4) . ?
C12 C20 1.506(4) . ?
C13 C14 1.372(4) . ?
C14 C15 1.404(4) . ?
C14 C21 1.500(4) . ?
C15 C16 1.409(4) . ?
C15 C19 1.510(4) . ?
F4 C42 1.340(3) . ?
F5 C42 1.340(3) . ?
F6 C42 1.349(3) . ?
C22 C23 1.397(4) . ?
C22 C27 1.409(4) . ?
C22 C31 1.425(4) . ?
C23 C24 1.404(4) . ?
C23 C37 1.467(4) . ?
C24 C25 1.429(4) . ?
C24 C38 1.494(4) . ?
C25 C26 1.345(5) . ?
C26 C27 1.409(5) . ?
C27 C28 1.419(5) . ?
C28 C29 1.348(5) . ?
C29 C30 1.409(5) . ?
C30 C31 1.389(4) . ?
C30 C39 1.506(5) . ?
C31 C32 1.515(4) . ?
C32 C33 1.396(4) . ?
C32 C37 1.423(4) . ?
C33 C34 1.387(4) . ?
C33 C40 1.515(4) . ?
C34 C35 1.405(4) . ?
C35 C36 1.389(4) . ?
C35 C42 1.493(4) . ?
C36 C37 1.413(4) . ?
C36 C41 1.504(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 123.1(2) . . ?
C6 C1 C10 124.5(2) . . ?
C2 C1 C10 112.4(2) . . ?
C3 C2 C1 118.5(2) . . ?
C3 C2 C16 135.5(2) . . ?
C1 C2 C16 105.7(2) . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 C17 126.2(3) . . ?
C4 C3 C17 116.4(3) . . ?
C5 C4 C3 123.5(3) . . ?
C4 C5 C6 120.5(3) . . ?
C1 C6 C7 115.8(3) . . ?
C1 C6 C5 116.5(3) . . ?
C7 C6 C5 127.7(3) . . ?
C8 C7 C6 120.1(3) . . ?
C7 C8 C9 124.5(3) . . ?
C10 C9 C8 117.2(3) . . ?
C10 C9 C18 126.1(3) . . ?
C8 C9 C18 116.6(3) . . ?
C9 C10 C1 117.8(2) . . ?
C9 C10 C11 136.9(3) . . ?
C1 C10 C11 105.2(2) . . ?
C12 C11 C16 120.1(2) . . ?
C12 C11 C10 132.4(2) . . ?
C16 C11 C10 107.5(2) . . ?
C13 C12 C11 116.9(2) . . ?
C13 C12 C20 116.6(2) . . ?
C11 C12 C20 126.4(3) . . ?
C14 C13 C12 122.8(3) . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 C21 118.3(3) . . ?
C15 C14 C21 120.1(3) . . ?
C14 C15 C16 116.3(2) . . ?
C14 C15 C19 121.7(2) . . ?
C16 C15 C19 121.6(2) . . ?
C15 C16 C11 120.7(2) . . ?
C15 C16 C2 130.5(2) . . ?
C11 C16 C2 108.5(2) . . ?
F1 C21 F2 106.0(2) . . ?
F1 C21 F3 105.6(2) . . ?
F2 C21 F3 105.8(3) . . ?
F1 C21 C14 113.0(3) . . ?
F2 C21 C14 112.9(2) . . ?
F3 C21 C14 113.0(2) . . ?
C23 C22 C27 124.1(3) . . ?
C23 C22 C31 112.9(2) . . ?
C27 C22 C31 122.9(3) . . ?
C22 C23 C24 118.2(2) . . ?
C22 C23 C37 106.1(2) . . ?
C24 C23 C37 135.4(3) . . ?
C23 C24 C25 116.9(3) . . ?
C23 C24 C38 126.9(3) . . ?
C25 C24 C38 115.9(3) . . ?
C26 C25 C24 123.6(3) . . ?
C25 C26 C27 120.8(3) . . ?
C26 C27 C22 115.9(3) . . ?
C26 C27 C28 127.3(3) . . ?
C22 C27 C28 116.8(3) . . ?
C29 C28 C27 119.0(3) . . ?
C28 C29 C30 125.7(3) . . ?
C31 C30 C29 116.8(3) . . ?
C31 C30 C39 127.2(3) . . ?
C29 C30 C39 116.0(3) . . ?
C30 C31 C22 118.7(3) . . ?
C30 C31 C32 137.0(3) . . ?
C22 C31 C32 104.2(2) . . ?
C33 C32 C37 120.9(2) . . ?
C33 C32 C31 132.0(2) . . ?
C37 C32 C31 107.1(2) . . ?
C34 C33 C32 117.0(2) . . ?
C34 C33 C40 116.5(2) . . ?
C32 C33 C40 126.4(2) . . ?
C33 C34 C35 122.1(2) . . ?
C36 C35 C34 121.6(2) . . ?
C36 C35 C42 120.6(2) . . ?
C34 C35 C42 117.8(2) . . ?
C35 C36 C37 116.5(2) . . ?
C35 C36 C41 120.8(2) . . ?
C37 C36 C41 122.4(2) . . ?
C36 C37 C32 120.6(2) . . ?
C36 C37 C23 130.5(2) . . ?
C32 C37 C23 108.8(2) . . ?
F4 C42 F5 106.3(2) . . ?
F4 C42 F6 105.4(2) . . ?
F5 C42 F6 105.4(2) . . ?
F4 C42 C35 112.8(2) . . ?
F5 C42 C35 113.6(2) . . ?
F6 C42 C35 112.7(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -9.6(4) . . . . ?
C10 C1 C2 C3 170.6(2) . . . . ?
C6 C1 C2 C16 176.1(2) . . . . ?
C10 C1 C2 C16 -3.7(3) . . . . ?
C1 C2 C3 C4 9.9(4) . . . . ?
C16 C2 C3 C4 -177.9(3) . . . . ?
C1 C2 C3 C17 -165.1(3) . . . . ?
C16 C2 C3 C17 7.2(5) . . . . ?
C2 C3 C4 C5 -3.9(4) . . . . ?
C17 C3 C4 C5 171.6(3) . . . . ?
C3 C4 C5 C6 -3.3(4) . . . . ?
C2 C1 C6 C7 -177.0(2) . . . . ?
C10 C1 C6 C7 2.8(4) . . . . ?
C2 C1 C6 C5 2.4(4) . . . . ?
C10 C1 C6 C5 -177.8(2) . . . . ?
C4 C5 C6 C1 4.0(4) . . . . ?
C4 C5 C6 C7 -176.7(3) . . . . ?
C1 C6 C7 C8 -0.3(4) . . . . ?
C5 C6 C7 C8 -179.7(3) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C7 C8 C9 C18 175.3(3) . . . . ?
C8 C9 C10 C1 3.8(4) . . . . ?
C18 C9 C10 C1 -172.9(3) . . . . ?
C8 C9 C10 C11 179.1(3) . . . . ?
C18 C9 C10 C11 2.4(5) . . . . ?
C6 C1 C10 C9 -4.7(4) . . . . ?
C2 C1 C10 C9 175.2(2) . . . . ?
C6 C1 C10 C11 178.7(2) . . . . ?
C2 C1 C10 C11 -1.5(3) . . . . ?
C9 C10 C11 C12 11.5(5) . . . . ?
C1 C10 C11 C12 -172.9(3) . . . . ?
C9 C10 C11 C16 -169.3(3) . . . . ?
C1 C10 C11 C16 6.3(3) . . . . ?
C16 C11 C12 C13 5.9(4) . . . . ?
C10 C11 C12 C13 -175.0(3) . . . . ?
C16 C11 C12 C20 -169.4(3) . . . . ?
C10 C11 C12 C20 9.7(5) . . . . ?
C11 C12 C13 C14 3.3(4) . . . . ?
C20 C12 C13 C14 179.0(3) . . . . ?
C12 C13 C14 C15 -4.2(4) . . . . ?
C12 C13 C14 C21 174.7(3) . . . . ?
C13 C14 C15 C16 -4.2(4) . . . . ?
C21 C14 C15 C16 176.9(2) . . . . ?
C13 C14 C15 C19 168.0(3) . . . . ?
C21 C14 C15 C19 -10.9(4) . . . . ?
C14 C15 C16 C11 13.2(3) . . . . ?
C19 C15 C16 C11 -158.9(2) . . . . ?
C14 C15 C16 C2 -173.1(2) . . . . ?
C19 C15 C16 C2 14.7(4) . . . . ?
C12 C11 C16 C15 -14.5(4) . . . . ?
C10 C11 C16 C15 166.2(2) . . . . ?
C12 C11 C16 C2 170.6(2) . . . . ?
C10 C11 C16 C2 -8.7(3) . . . . ?
C3 C2 C16 C15 20.6(5) . . . . ?
C1 C2 C16 C15 -166.5(3) . . . . ?
C3 C2 C16 C11 -165.2(3) . . . . ?
C1 C2 C16 C11 7.7(3) . . . . ?
C13 C14 C21 F1 16.1(4) . . . . ?
C15 C14 C21 F1 -164.9(2) . . . . ?
C13 C14 C21 F2 136.3(3) . . . . ?
C15 C14 C21 F2 -44.8(4) . . . . ?
C13 C14 C21 F3 -103.7(3) . . . . ?
C15 C14 C21 F3 75.2(3) . . . . ?
C27 C22 C23 C24 8.4(4) . . . . ?
C31 C22 C23 C24 -170.8(2) . . . . ?
C27 C22 C23 C37 -177.2(2) . . . . ?
C31 C22 C23 C37 3.5(3) . . . . ?
C22 C23 C24 C25 -6.7(4) . . . . ?
C37 C23 C24 C25 -178.9(3) . . . . ?
C22 C23 C24 C38 167.3(3) . . . . ?
C37 C23 C24 C38 -4.9(5) . . . . ?
C23 C24 C25 C26 1.1(4) . . . . ?
C38 C24 C25 C26 -173.6(3) . . . . ?
C24 C25 C26 C27 3.5(5) . . . . ?
C25 C26 C27 C22 -2.1(5) . . . . ?
C25 C26 C27 C28 177.5(3) . . . . ?
C23 C22 C27 C26 -4.0(4) . . . . ?
C31 C22 C27 C26 175.2(3) . . . . ?
C23 C22 C27 C28 176.4(3) . . . . ?
C31 C22 C27 C28 -4.4(4) . . . . ?
C26 C27 C28 C29 -178.9(3) . . . . ?
C22 C27 C28 C29 0.6(4) . . . . ?
C27 C28 C29 C30 1.3(5) . . . . ?
C28 C29 C30 C31 0.5(5) . . . . ?
C28 C29 C30 C39 -177.4(3) . . . . ?
C29 C30 C31 C22 -4.1(4) . . . . ?
C39 C30 C31 C22 173.5(3) . . . . ?
C29 C30 C31 C32 -179.4(3) . . . . ?
C39 C30 C31 C32 -1.7(6) . . . . ?
C23 C22 C31 C30 -174.5(2) . . . . ?
C27 C22 C31 C30 6.2(4) . . . . ?
C23 C22 C31 C32 2.2(3) . . . . ?
C27 C22 C31 C32 -177.1(2) . . . . ?
C30 C31 C32 C33 -11.0(5) . . . . ?
C22 C31 C32 C33 173.2(3) . . . . ?
C30 C31 C32 C37 168.5(3) . . . . ?
C22 C31 C32 C37 -7.2(3) . . . . ?
C37 C32 C33 C34 -4.6(4) . . . . ?
C31 C32 C33 C34 174.9(2) . . . . ?
C37 C32 C33 C40 172.2(2) . . . . ?
C31 C32 C33 C40 -8.3(4) . . . . ?
C32 C33 C34 C35 -2.8(4) . . . . ?
C40 C33 C34 C35 -180.0(2) . . . . ?
C33 C34 C35 C36 2.5(4) . . . . ?
C33 C34 C35 C42 -176.7(2) . . . . ?
C34 C35 C36 C37 5.2(4) . . . . ?
C42 C35 C36 C37 -175.7(2) . . . . ?
C34 C35 C36 C41 -168.6(2) . . . . ?
C42 C35 C36 C41 10.5(4) . . . . ?
C35 C36 C37 C32 -12.5(4) . . . . ?
C41 C36 C37 C32 161.2(2) . . . . ?
C35 C36 C37 C23 171.9(2) . . . . ?
C41 C36 C37 C23 -14.5(4) . . . . ?
C33 C32 C37 C36 12.6(4) . . . . ?
C31 C32 C37 C36 -167.0(2) . . . . ?
C33 C32 C37 C23 -170.9(2) . . . . ?
C31 C32 C37 C23 9.5(3) . . . . ?
C22 C23 C37 C36 167.9(3) . . . . ?
C24 C23 C37 C36 -19.2(5) . . . . ?
C22 C23 C37 C32 -8.2(3) . . . . ?
C24 C23 C37 C32 164.7(3) . . . . ?
C36 C35 C42 F4 -74.8(3) . . . . ?
C34 C35 C42 F4 104.4(3) . . . . ?
C36 C35 C42 F5 46.3(3) . . . . ?
C34 C35 C42 F5 -134.5(3) . . . . ?
C36 C35 C42 F6 166.0(2) . . . . ?
C34 C35 C42 F6 -14.8(4) . . . . ?

_refine_diff_density_max         0.494
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.052

