# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_KM2
_database_code_depnum_ccdc_archive 'CCDC 1552782'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 F5 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         454.43
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   37.637(3)
_cell_length_b                   4.9401(5)
_cell_length_c                   11.5774(11)
_cell_angle_alpha                90
_cell_angle_beta                 94.936(3)
_cell_angle_gamma                90
_cell_volume                     2144.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3009
_cell_measurement_theta_min      3.2597
_cell_measurement_theta_max      26.0270
_cell_measurement_temperature    273.0(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936

_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.46516
_exptl_absorpt_correction_T_max  1.00000

_exptl_special_details           
;
;

_diffrn_ambient_temperature      273.0(2)

_diffrn_source                   ?
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            6925
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         26.18
_diffrn_reflns_theta_full        26.18
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3712
_reflns_number_gt                3028
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1265
_refine_ls_goodness_of_fit_ref   0.876
_refine_ls_restrained_S_all      0.876
_refine_ls_number_reflns         3712
_refine_ls_number_parameters     299
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.152
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1084 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F001 0.61590(6) -0.6603(5) 0.9416(2) 0.0578(6) Uani d . . . 1 . .
C C1 0.27396(19) 1.7992(16) 0.0053(7) 0.109(2) Uani d . . . 1 . .
H H1A 0.2673 1.9131 -0.0602 0.163 Uiso calc U . R 1 . .
H H1B 0.2531 1.7548 0.0437 0.163 Uiso calc U . R 1 . .
H H1C 0.2846 1.636 -0.0205 0.163 Uiso calc U . R 1 . .
F F002 0.66316(8) -1.0578(5) 0.9936(2) 0.0634(7) Uani d . . . 1 . .
C C2 0.30007(15) 1.9450(13) 0.0877(6) 0.0871(17) Uani d . . . 1 . .
H H2A 0.3182 2.0261 0.0441 0.105 Uiso calc U . R 1 . .
H H2B 0.2878 2.0904 0.124 0.105 Uiso calc U . R 1 . .
F F003 0.71901(7) -1.1288(5) 0.8643(3) 0.0703(8) Uani d . . . 1 . .
C C3 0.31785(12) 1.7689(10) 0.1803(5) 0.0676(12) Uani d . . . 1 . .
H H3A 0.3315 1.6308 0.1443 0.081 Uiso calc U . R 1 . .
H H3B 0.2997 1.6783 0.2206 0.081 Uiso calc U . R 1 . .
F F004 0.67898(7) -0.4087(5) 0.6256(2) 0.0657(7) Uani d . . . 1 . .
C C4 0.34237(12) 1.9224(9) 0.2677(5) 0.0661(13) Uani d . . . 1 . .
H H4A 0.3284 2.0532 0.3069 0.079 Uiso calc U . R 1 . .
H H4B 0.3596 2.022 0.2268 0.079 Uiso calc U . R 1 . .
O O005 0.38805(7) 1.5966(6) 0.2997(3) 0.0536(7) Uani d . . . 1 . .
C C5 0.36222(11) 1.7429(9) 0.3580(4) 0.0591(11) Uani d . . . 1 . .
H H5A 0.3738 1.8518 0.4199 0.071 Uiso calc U . R 1 . .
H H5B 0.3458 1.619 0.391 0.071 Uiso calc U . R 1 . .
F F006 0.72636(7) -0.8035(7) 0.6802(3) 0.0802(9) Uani d . . . 1 . .
C C6 0.40999(9) 1.4234(7) 0.3636(3) 0.0418(8) Uani d . . . 1 . .
C C7 0.40843(9) 1.3658(7) 0.4801(4) 0.0442(8) Uani d . . . 1 . .
H H7 0.3918 1.4526 0.5223 0.053 Uiso calc U . R 1 . .
C C8 0.43189(9) 1.1769(7) 0.5336(3) 0.0422(8) Uani d . . . 1 . .
H H8 0.4309 1.1396 0.612 0.051 Uiso calc U . R 1 . .
C C9 0.45679(9) 1.0430(7) 0.4725(3) 0.0379(7) Uani d . . . 1 . .
C C10 0.45828(9) 1.1104(8) 0.3552(3) 0.0452(9) Uani d . . . 1 . .
H H10 0.4753 1.0282 0.3131 0.054 Uiso calc U . R 1 . .
C C11 0.43519(10) 1.2950(7) 0.3015(3) 0.0444(8) Uani d . . . 1 . .
H H11 0.4364 1.3345 0.2234 0.053 Uiso calc U . R 1 . .
C C12 0.48036(9) 0.8424(7) 0.5248(3) 0.0388(8) Uani d . . . 1 . .
C C13 0.50041(9) 0.6716(7) 0.5635(3) 0.0380(7) Uani d . . . 1 . .
C C14 0.52474(8) 0.4641(6) 0.6070(3) 0.0344(7) Uani d . . . 1 . .
C C15 0.52417(9) 0.3573(7) 0.7175(3) 0.0385(7) Uani d . . . 1 . .
H H15 0.5078 0.4225 0.7663 0.046 Uiso calc U . R 1 . .
C C16 0.54768(9) 0.1550(7) 0.7563(3) 0.0387(8) Uani d . . . 1 . .
H H16 0.5466 0.0835 0.8302 0.046 Uiso calc U . R 1 . .
C C17 0.57292(8) 0.0578(6) 0.6857(3) 0.0347(7) Uani d . . . 1 . .
C C18 0.57371(9) 0.1667(7) 0.5745(3) 0.0406(8) Uani d . . . 1 . .
H H18 0.5905 0.1042 0.5265 0.049 Uiso calc U . R 1 . .
C C19 0.54992(9) 0.3654(7) 0.5350(3) 0.0396(8) Uani d . . . 1 . .
H H19 0.5506 0.4341 0.4604 0.047 Uiso calc U . R 1 . .
C C20 0.59809(9) -0.1500(6) 0.7230(3) 0.0373(7) Uani d . . . 1 . .
C C21 0.61943(9) -0.3194(7) 0.7511(3) 0.0385(7) Uani d . . . 1 . .
C C22 0.64570(9) -0.5225(7) 0.7816(3) 0.0356(7) Uani d . . . 1 . .
C C23 0.67448(9) -0.5665(7) 0.7171(3) 0.0423(8) Uani d . . . 1 . .
C C24 0.69932(9) -0.7657(8) 0.7441(4) 0.0489(9) Uani d . . . 1 . .
C C25 0.69562(10) -0.9304(8) 0.8390(4) 0.0470(9) Uani d . . . 1 . .
C C26 0.66760(10) -0.8916(7) 0.9047(3) 0.0428(8) Uani d . . . 1 . .
C C27 0.64320(8) -0.6901(7) 0.8765(3) 0.0372(7) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F001 C27 . 1.333(4) ?
C1 C2 . 1.494(9) ?
C1 H1A . 0.96 ?
C1 H1B . 0.96 ?
C1 H1C . 0.96 ?
F002 C26 . 1.338(4) ?
C2 C3 . 1.493(7) ?
C2 H2A . 0.97 ?
C2 H2B . 0.97 ?
F003 C25 . 1.333(4) ?
C3 C4 . 1.514(7) ?
C3 H3A . 0.97 ?
C3 H3B . 0.97 ?
F004 C23 . 1.337(4) ?
C4 C5 . 1.517(6) ?
C4 H4A . 0.97 ?
C4 H4B . 0.97 ?
O005 C6 . 1.363(4) ?
O005 C5 . 1.427(5) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
F006 C24 . 1.322(5) ?
C6 C7 . 1.384(5) ?
C6 C11 . 1.392(5) ?
C7 C8 . 1.393(5) ?
C7 H7 . 0.93 ?
C8 C9 . 1.389(5) ?
C8 H8 . 0.93 ?
C9 C10 . 1.404(5) ?
C9 C12 . 1.429(5) ?
C10 C11 . 1.372(5) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C12 C13 . 1.193(5) ?
C13 C14 . 1.437(4) ?
C14 C15 . 1.385(5) ?
C14 C19 . 1.403(5) ?
C15 C16 . 1.384(5) ?
C15 H15 . 0.93 ?
C16 C17 . 1.391(5) ?
C16 H16 . 0.93 ?
C17 C18 . 1.398(5) ?
C17 C20 . 1.438(4) ?
C18 C19 . 1.380(5) ?
C18 H18 . 0.93 ?
C19 H19 . 0.93 ?
C20 C21 . 1.186(5) ?
C21 C22 . 1.432(5) ?
C22 C23 . 1.385(5) ?
C22 C27 . 1.385(5) ?
C23 C24 . 1.375(5) ?
C24 C25 . 1.384(6) ?
C25 C26 . 1.366(6) ?
C26 C27 . 1.375(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C3 C2 C1 . . 114.0(5) ?
C3 C2 H2A . . 108.8 ?
C1 C2 H2A . . 108.8 ?
C3 C2 H2B . . 108.8 ?
C1 C2 H2B . . 108.8 ?
H2A C2 H2B . . 107.6 ?
C2 C3 C4 . . 113.5(4) ?
C2 C3 H3A . . 108.9 ?
C4 C3 H3A . . 108.9 ?
C2 C3 H3B . . 108.9 ?
C4 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
C3 C4 C5 . . 113.8(4) ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4B . . 108.8 ?
C5 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
C6 O005 C5 . . 117.8(3) ?
O005 C5 C4 . . 106.6(4) ?
O005 C5 H5A . . 110.4 ?
C4 C5 H5A . . 110.4 ?
O005 C5 H5B . . 110.4 ?
C4 C5 H5B . . 110.4 ?
H5A C5 H5B . . 108.6 ?
O005 C6 C7 . . 125.7(3) ?
O005 C6 C11 . . 114.4(3) ?
C7 C6 C11 . . 119.9(3) ?
C6 C7 C8 . . 119.5(3) ?
C6 C7 H7 . . 120.3 ?
C8 C7 H7 . . 120.3 ?
C9 C8 C7 . . 121.5(3) ?
C9 C8 H8 . . 119.2 ?
C7 C8 H8 . . 119.2 ?
C8 C9 C10 . . 117.7(3) ?
C8 C9 C12 . . 122.4(3) ?
C10 C9 C12 . . 119.9(3) ?
C11 C10 C9 . . 121.3(3) ?
C11 C10 H10 . . 119.3 ?
C9 C10 H10 . . 119.3 ?
C10 C11 C6 . . 120.1(4) ?
C10 C11 H11 . . 119.9 ?
C6 C11 H11 . . 119.9 ?
C13 C12 C9 . . 177.0(4) ?
C12 C13 C14 . . 178.5(4) ?
C15 C14 C19 . . 118.8(3) ?
C15 C14 C13 . . 122.4(3) ?
C19 C14 C13 . . 118.8(3) ?
C16 C15 C14 . . 121.0(3) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C17 . . 120.6(3) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C16 C17 C18 . . 118.6(3) ?
C16 C17 C20 . . 122.4(3) ?
C18 C17 C20 . . 119.0(3) ?
C19 C18 C17 . . 121.0(3) ?
C19 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
C18 C19 C14 . . 120.2(3) ?
C18 C19 H19 . . 119.9 ?
C14 C19 H19 . . 119.9 ?
C21 C20 C17 . . 178.0(4) ?
C20 C21 C22 . . 178.2(4) ?
C23 C22 C27 . . 116.3(3) ?
C23 C22 C21 . . 122.2(3) ?
C27 C22 C21 . . 121.5(3) ?
F004 C23 C24 . . 117.9(3) ?
F004 C23 C22 . . 119.6(3) ?
C24 C23 C22 . . 122.5(3) ?
F006 C24 C23 . . 121.0(4) ?
F006 C24 C25 . . 119.8(4) ?
C23 C24 C25 . . 119.2(3) ?
F003 C25 C26 . . 120.5(4) ?
F003 C25 C24 . . 119.8(4) ?
C26 C25 C24 . . 119.7(3) ?
F002 C26 C25 . . 119.7(3) ?
F002 C26 C27 . . 120.1(3) ?
C25 C26 C27 . . 120.1(3) ?
F001 C27 C26 . . 118.5(3) ?
F001 C27 C22 . . 119.4(3) ?
C26 C27 C22 . . 122.1(3) ?

####################################################################### 
# 
# 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_sy-217
_database_code_depnum_ccdc_archive 'CCDC 1552781'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-26 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         'C23 H11 F5 O'
_chemical_formula_sum            'C23 H11 F5 O'
_chemical_formula_weight         398.32

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'
O O 0.0106 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.0030(5)
_cell_length_b                   7.6051(7)
_cell_length_c                   40.901(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.432(8)
_cell_angle_gamma                90
_cell_volume                     1865.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5043
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      24.70

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   0.974
_exptl_transmission_factor_max   0.979
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.120
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46516
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.572
_oxdiff_exptl_absorpt_empirical_full_max 2.998
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15404
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         2.724
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3469
_reflns_number_gt                2097
_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
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_computing_publication_material  
;
Yadokari-XG 2014 (Wakita, Nemoto, et al., 2016)
;
_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)+(0.1032P)²] 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         3469
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.2093
_refine_ls_wR_factor_gt          0.1675
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 1.2804(5) 0.5787(5) 0.20020(8) 0.0881(10) Uani 1 1 d . . . . .
H1 H 1.4104 0.6289 0.2110 0.132 Uiso 1 1 calc R U . . .
H2 H 1.2927 0.5879 0.1769 0.132 Uiso 1 1 calc R U . . .
H3 H 1.2685 0.4571 0.2062 0.132 Uiso 1 1 calc R U . . .
O1 O 1.0858(3) 0.6714(3) 0.20980(5) 0.0746(6) Uani 1 1 d . . . . .
C2 C 1.0341(4) 0.6682(3) 0.24172(6) 0.0585(7) Uani 1 1 d . . . . .
C3 C 0.8423(4) 0.7594(4) 0.24941(7) 0.0689(8) Uani 1 1 d . . . . .
H4 H 0.7589 0.8173 0.2330 0.083 Uiso 1 1 calc R U . . .
C4 C 0.7761(4) 0.7641(4) 0.28087(8) 0.0703(8) Uani 1 1 d . . . . .
H5 H 0.6477 0.8257 0.2856 0.084 Uiso 1 1 calc R U . . .
C5 C 0.8970(5) 0.6784(3) 0.30610(7) 0.0648(7) Uani 1 1 d . . . . .
C6 C 1.0873(5) 0.5872(4) 0.29813(7) 0.0667(7) Uani 1 1 d . . . . .
H6 H 1.1703 0.5287 0.3145 0.080 Uiso 1 1 calc R U . . .
C7 C 1.1557(4) 0.5818(4) 0.26633(7) 0.0638(7) Uani 1 1 d . . . . .
H7 H 1.2837 0.5199 0.2614 0.077 Uiso 1 1 calc R U . . .
C8 C 0.8274(5) 0.6898(4) 0.33914(8) 0.0718(8) Uani 1 1 d . . . . .
C9 C 0.7698(5) 0.7027(4) 0.36682(8) 0.0710(8) Uani 1 1 d . . . . .
C10 C 0.7010(4) 0.7175(3) 0.39940(7) 0.0634(7) Uani 1 1 d . . . . .
C11 C 0.4936(4) 0.7886(4) 0.40647(7) 0.0677(7) Uani 1 1 d . . . . .
H8 H 0.3982 0.8276 0.3895 0.081 Uiso 1 1 calc R U . . .
C12 C 0.4293(4) 0.8013(4) 0.43820(7) 0.0668(7) Uani 1 1 d . . . . .
H9 H 0.2910 0.8493 0.4424 0.080 Uiso 1 1 calc R U . . .
C13 C 0.5668(4) 0.7437(3) 0.46410(7) 0.0622(7) Uani 1 1 d . . . . .
C14 C 0.7755(5) 0.6728(4) 0.45715(8) 0.0709(8) Uani 1 1 d . . . . .
H10 H 0.8701 0.6331 0.4742 0.085 Uiso 1 1 calc R U . . .
C15 C 0.8409(5) 0.6613(4) 0.42557(7) 0.0689(8) Uani 1 1 d . . . . .
H11 H 0.9806 0.6155 0.4214 0.083 Uiso 1 1 calc R U . . .
C16 C 0.4980(5) 0.7544(3) 0.49709(8) 0.0657(7) Uani 1 1 d . . . . .
C17 C 0.4389(5) 0.7605(4) 0.52454(7) 0.0647(7) Uani 1 1 d . . . . .
C18 C 0.3778(4) 0.7664(3) 0.55775(6) 0.0573(7) Uani 1 1 d . . . . .
C19 C 0.1782(4) 0.8397(3) 0.56728(7) 0.0597(7) Uani 1 1 d . . . . .
C20 C 0.1240(4) 0.8468(3) 0.59943(7) 0.0621(7) Uani 1 1 d . . . . .
C21 C 0.2643(4) 0.7791(4) 0.62339(7) 0.0663(7) Uani 1 1 d . . . . .
C22 C 0.4647(4) 0.7051(4) 0.61488(7) 0.0653(7) Uani 1 1 d . . . . .
C23 C 0.5171(4) 0.6998(3) 0.58281(7) 0.0601(7) Uani 1 1 d . . . . .
F1 F 0.0353(3) 0.9055(2) 0.54452(4) 0.0827(5) Uani 1 1 d . . . . .
F2 F -0.0691(2) 0.9213(2) 0.60782(4) 0.0867(6) Uani 1 1 d . . . . .
F3 F 0.2096(3) 0.7856(3) 0.65452(4) 0.0990(7) Uani 1 1 d . . . . .
F4 F 0.6030(3) 0.6375(3) 0.63796(4) 0.0988(7) Uani 1 1 d . . . . .
F5 F 0.7113(2) 0.6259(2) 0.57491(4) 0.0840(6) 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 O1 1.434(3) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
O1 C2 1.355(3) . ?
C2 C7 1.384(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.363(4) . ?
C3 H4 0.9300 . ?
C4 C5 1.398(4) . ?
C4 H5 0.9300 . ?
C5 C6 1.387(4) . ?
C5 C8 1.434(4) . ?
C6 C7 1.381(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.202(4) . ?
C9 C10 1.416(4) . ?
C10 C15 1.399(4) . ?
C10 C11 1.398(4) . ?
C11 C12 1.373(4) . ?
C11 H8 0.9300 . ?
C12 C13 1.386(4) . ?
C12 H9 0.9300 . ?
C13 C14 1.404(4) . ?
C13 C16 1.430(4) . ?
C14 C15 1.369(4) . ?
C14 H10 0.9300 . ?
C15 H11 0.9300 . ?
C16 C17 1.193(4) . ?
C17 C18 1.423(4) . ?
C18 C19 1.392(3) . ?
C18 C23 1.390(4) . ?
C19 F1 1.336(3) . ?
C19 C20 1.369(3) . ?
C20 F2 1.348(3) . ?
C20 C21 1.365(4) . ?
C21 F3 1.329(3) . ?
C21 C22 1.386(4) . ?
C22 F4 1.333(3) . ?
C22 C23 1.362(4) . ?
C23 F5 1.346(3) . ?

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
O1 C1 H1 109.5 . . ?
O1 C1 H2 109.5 . . ?
H1 C1 H2 109.5 . . ?
O1 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C2 O1 C1 118.5(2) . . ?
O1 C2 C7 125.1(2) . . ?
O1 C2 C3 115.7(2) . . ?
C7 C2 C3 119.2(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H4 119.9 . . ?
C2 C3 H4 119.9 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H5 119.3 . . ?
C5 C4 H5 119.3 . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C8 121.8(3) . . ?
C4 C5 C8 120.3(3) . . ?
C7 C6 C5 121.1(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
C9 C8 C5 178.7(3) . . ?
C8 C9 C10 179.7(3) . . ?
C15 C10 C11 118.1(3) . . ?
C15 C10 C9 120.4(3) . . ?
C11 C10 C9 121.5(3) . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H8 119.6 . . ?
C10 C11 H8 119.6 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H9 119.4 . . ?
C13 C12 H9 119.4 . . ?
C12 C13 C14 118.3(3) . . ?
C12 C13 C16 121.1(2) . . ?
C14 C13 C16 120.6(3) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H10 119.7 . . ?
C13 C14 H10 119.7 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H11 119.5 . . ?
C10 C15 H11 119.5 . . ?
C17 C16 C13 178.8(3) . . ?
C16 C17 C18 177.6(3) . . ?
C19 C18 C23 115.9(2) . . ?
C19 C18 C17 122.7(2) . . ?
C23 C18 C17 121.4(2) . . ?
F1 C19 C20 118.9(2) . . ?
F1 C19 C18 119.3(2) . . ?
C20 C19 C18 121.8(2) . . ?
F2 C20 C21 119.1(2) . . ?
F2 C20 C19 120.2(2) . . ?
C21 C20 C19 120.7(2) . . ?
F3 C21 C20 120.3(2) . . ?
F3 C21 C22 120.5(3) . . ?
C20 C21 C22 119.2(3) . . ?
F4 C22 C23 120.5(3) . . ?
F4 C22 C21 120.0(3) . . ?
C23 C22 C21 119.5(3) . . ?
F5 C23 C22 118.7(2) . . ?
F5 C23 C18 118.4(2) . . ?
C22 C23 C18 122.9(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
C1 O1 C2 C7 0.2(4) . . . . ?
C1 O1 C2 C3 -179.4(2) . . . . ?
O1 C2 C3 C4 -180.0(2) . . . . ?
C7 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C3 C4 C5 C8 178.2(3) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
C8 C5 C6 C7 -178.1(3) . . . . ?
C5 C6 C7 C2 0.0(4) . . . . ?
O1 C2 C7 C6 -180.0(2) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C15 C10 C11 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 179.7(2) . . . . ?
C10 C11 C12 C13 -0.3(4) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C11 C12 C13 C16 -179.0(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C16 C13 C14 C15 179.5(2) . . . . ?
C13 C14 C15 C10 -0.9(4) . . . . ?
C11 C10 C15 C14 1.1(4) . . . . ?
C9 C10 C15 C14 -179.2(2) . . . . ?
C23 C18 C19 F1 -179.7(2) . . . . ?
C17 C18 C19 F1 0.9(4) . . . . ?
C23 C18 C19 C20 0.6(4) . . . . ?
C17 C18 C19 C20 -178.9(2) . . . . ?
F1 C19 C20 F2 -0.9(4) . . . . ?
C18 C19 C20 F2 178.9(2) . . . . ?
F1 C19 C20 C21 179.2(2) . . . . ?
C18 C19 C20 C21 -1.0(4) . . . . ?
F2 C20 C21 F3 0.6(4) . . . . ?
C19 C20 C21 F3 -179.6(2) . . . . ?
F2 C20 C21 C22 -178.9(2) . . . . ?
C19 C20 C21 C22 1.0(4) . . . . ?
F3 C21 C22 F4 0.9(4) . . . . ?
C20 C21 C22 F4 -179.6(3) . . . . ?
F3 C21 C22 C23 179.9(2) . . . . ?
C20 C21 C22 C23 -0.6(4) . . . . ?
F4 C22 C23 F5 -0.3(4) . . . . ?
C21 C22 C23 F5 -179.3(2) . . . . ?
F4 C22 C23 C18 179.2(2) . . . . ?
C21 C22 C23 C18 0.2(4) . . . . ?
C19 C18 C23 F5 179.3(2) . . . . ?
C17 C18 C23 F5 -1.2(4) . . . . ?
C19 C18 C23 C22 -0.2(4) . . . . ?
C17 C18 C23 C22 179.3(2) . . . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/methanol'
