# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_xyw-1
_database_code_depnum_ccdc_archive 'CCDC 1444225'
_audit_update_record             
;
2015-12-25 deposited with the CCDC.
2016-05-31 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 H15 F O4'
_chemical_formula_weight         362.34

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'
O O 0.0106 0.0060 '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           Triclinic
_symmetry_space_group_name_H-M   'P-1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2368(3)
_cell_length_b                   12.0269(5)
_cell_length_c                   12.3293(6)
_cell_angle_alpha                107.207(2)
_cell_angle_beta                 92.248(2)
_cell_angle_gamma                98.168(2)
_cell_volume                     871.22(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1736
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      29.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15375
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         29.57
_reflns_number_total             4728
_reflns_number_gt                3008
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.036(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4728
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0946
_refine_ls_wR_factor_ref         0.3526
_refine_ls_wR_factor_gt          0.3069
_refine_ls_goodness_of_fit_ref   1.338
_refine_ls_restrained_S_all      1.338
_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
O1 O 0.0399(3) 0.33008(13) 0.84234(16) 0.0567(5) Uani 1 1 d . . .
O4 O 0.0293(3) -0.35260(14) 0.60326(17) 0.0692(6) Uani 1 1 d . . .
O3 O -0.6184(4) 0.16791(17) 1.05609(19) 0.0735(6) Uani 1 1 d . . .
C4 C -0.3297(4) 0.1212(2) 0.9275(2) 0.0552(6) Uani 1 1 d . . .
H4 H -0.3547 0.0404 0.9165 0.066 Uiso 1 1 calc R . .
C1 C 0.1146(4) 0.2273(2) 0.7833(2) 0.0514(6) Uani 1 1 d . . .
C9 C -0.1317(4) 0.29767(19) 0.8986(2) 0.0522(6) Uani 1 1 d . . .
C2 C -0.0063(4) 0.13112(18) 0.8010(2) 0.0508(6) Uani 1 1 d . . .
C3 C -0.1660(4) 0.17467(18) 0.8764(2) 0.0490(6) Uani 1 1 d . . .
C5 C -0.4494(5) 0.1959(2) 0.9945(2) 0.0550(6) Uani 1 1 d . . .
C10 C 0.3024(4) 0.2468(2) 0.7197(2) 0.0549(6) Uani 1 1 d . . .
O2 O -0.5603(4) 0.36866(16) 1.0832(2) 0.0783(7) Uani 1 1 d . . .
C16 C 0.0091(4) 0.00427(19) 0.7510(2) 0.0489(6) Uani 1 1 d . . .
C8 C -0.2521(5) 0.3738(2) 0.9665(2) 0.0590(7) Uani 1 1 d . . .
H8 H -0.2259 0.4550 0.9796 0.071 Uiso 1 1 calc R . .
C7 C -0.4153(5) 0.3177(2) 1.0130(2) 0.0576(6) Uani 1 1 d . . .
C19 C 0.0298(4) -0.23571(18) 0.6570(2) 0.0520(6) Uani 1 1 d . . .
C11 C 0.3925(5) 0.1531(3) 0.6514(3) 0.0681(8) Uani 1 1 d . . .
H11 H 0.3326 0.0758 0.6447 0.082 Uiso 1 1 calc R . .
C6 C -0.6995(5) 0.2738(2) 1.1058(3) 0.0674(8) Uani 1 1 d . . .
H6A H -0.7022 0.2881 1.1873 0.081 Uiso 1 1 calc R . .
H6B H -0.8465 0.2680 1.0736 0.081 Uiso 1 1 calc R . .
C15 C 0.3962(6) 0.3601(2) 0.7276(3) 0.0732(8) Uani 1 1 d . . .
H15 H 0.3387 0.4238 0.7726 0.088 Uiso 1 1 calc R . .
C13 C 0.6674(5) 0.2868(3) 0.6030(3) 0.0723(8) Uani 1 1 d . . .
H13 H 0.7913 0.3010 0.5665 0.087 Uiso 1 1 calc R . .
C12 C 0.5733(6) 0.1764(3) 0.5934(3) 0.0744(8) Uani 1 1 d . . .
H12 H 0.6301 0.1134 0.5467 0.089 Uiso 1 1 calc R . .
C20 C 0.1563(6) -0.1697(2) 0.7519(3) 0.0820(11) Uani 1 1 d . . .
H20 H 0.2525 -0.2040 0.7863 0.098 Uiso 1 1 calc R . .
C21 C 0.1438(6) -0.0514(2) 0.7984(3) 0.0839(11) Uani 1 1 d . . .
H21 H 0.2309 -0.0082 0.8645 0.101 Uiso 1 1 calc R . .
C18 C -0.1174(7) -0.1838(3) 0.6114(3) 0.0990(14) Uani 1 1 d . . .
H18 H -0.2114 -0.2286 0.5484 0.119 Uiso 1 1 calc R . .
F1 F 0.6621(7) 0.4870(2) 0.6780(3) 0.1703(18) Uani 1 1 d . . .
C22 C 0.1737(7) -0.4097(3) 0.6471(4) 0.0997(13) Uani 1 1 d . . .
H22A H 0.3191 -0.3826 0.6330 0.150 Uiso 1 1 calc R . .
H22B H 0.1379 -0.4933 0.6109 0.150 Uiso 1 1 calc R . .
H22C H 0.1637 -0.3928 0.7277 0.150 Uiso 1 1 calc R . .
C17 C -0.1269(7) -0.0659(3) 0.6582(3) 0.1044(15) Uani 1 1 d . . .
H17 H -0.2283 -0.0325 0.6260 0.125 Uiso 1 1 calc R . .
C14 C 0.5727(7) 0.3795(3) 0.6698(3) 0.0852(10) 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
O1 C9 1.370(3) . ?
O1 C1 1.390(3) . ?
O4 C19 1.365(2) . ?
O4 C22 1.390(4) . ?
O3 C5 1.383(3) . ?
O3 C6 1.414(3) . ?
C4 C5 1.358(4) . ?
C4 C3 1.398(4) . ?
C1 C2 1.367(3) . ?
C1 C10 1.465(4) . ?
C9 C8 1.376(3) . ?
C9 C3 1.405(3) . ?
C2 C3 1.437(4) . ?
C2 C16 1.485(3) . ?
C5 C7 1.398(3) . ?
C10 C15 1.378(4) . ?
C10 C11 1.396(4) . ?
O2 C7 1.359(3) . ?
O2 C6 1.434(3) . ?
C16 C21 1.359(4) . ?
C16 C17 1.375(4) . ?
C8 C7 1.379(4) . ?
C19 C20 1.350(4) . ?
C19 C18 1.372(4) . ?
C11 C12 1.398(5) . ?
C15 C14 1.365(5) . ?
C13 C12 1.342(5) . ?
C13 C14 1.397(5) . ?
C20 C21 1.382(4) . ?
C18 C17 1.374(4) . ?
F1 C14 1.305(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
C9 O1 C1 107.03(18) . . ?
C19 O4 C22 118.2(2) . . ?
C5 O3 C6 106.4(2) . . ?
C5 C4 C3 115.2(2) . . ?
C2 C1 O1 110.6(2) . . ?
C2 C1 C10 135.3(2) . . ?
O1 C1 C10 114.0(2) . . ?
O1 C9 C8 125.3(2) . . ?
O1 C9 C3 109.6(2) . . ?
C8 C9 C3 125.2(2) . . ?
C1 C2 C3 106.6(2) . . ?
C1 C2 C16 129.1(2) . . ?
C3 C2 C16 124.3(2) . . ?
C4 C3 C9 119.9(2) . . ?
C4 C3 C2 133.9(2) . . ?
C9 C3 C2 106.2(2) . . ?
C4 C5 O3 127.7(2) . . ?
C4 C5 C7 123.7(2) . . ?
O3 C5 C7 108.6(2) . . ?
C15 C10 C11 118.4(3) . . ?
C15 C10 C1 119.8(2) . . ?
C11 C10 C1 121.8(2) . . ?
C7 O2 C6 106.0(2) . . ?
C21 C16 C17 116.0(2) . . ?
C21 C16 C2 122.8(2) . . ?
C17 C16 C2 121.0(2) . . ?
C9 C8 C7 113.2(2) . . ?
O2 C7 C8 127.0(2) . . ?
O2 C7 C5 110.3(2) . . ?
C8 C7 C5 122.7(2) . . ?
C20 C19 O4 125.7(2) . . ?
C20 C19 C18 118.3(2) . . ?
O4 C19 C18 116.0(2) . . ?
C10 C11 C12 119.6(3) . . ?
O3 C6 O2 108.4(2) . . ?
C14 C15 C10 120.4(3) . . ?
C12 C13 C14 117.7(3) . . ?
C13 C12 C11 122.0(3) . . ?
C19 C20 C21 120.5(2) . . ?
C16 C21 C20 122.5(2) . . ?
C19 C18 C17 120.4(2) . . ?
C18 C17 C16 122.0(3) . . ?
F1 C14 C15 120.3(3) . . ?
F1 C14 C13 117.9(3) . . ?
C15 C14 C13 121.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.966
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 0.966
_refine_diff_density_max         1.606
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.106
