# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1518214'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F O2'
_chemical_formula_weight         268.27

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   10.848(2)
_cell_length_b                   8.1961(16)
_cell_length_c                   15.304(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.597(3)
_cell_angle_gamma                90.00
_cell_volume                     1322.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3837
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      30.86

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9762
_exptl_absorpt_process_details   SADABS

_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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6421
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_sigmaI/netI    0.0513
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2326
_reflns_number_gt                2058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0620P)²+0.2951P] 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       0.158(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1179
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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 0.36317(13) 0.47758(17) 0.12333(9) 0.0370(4) Uani 1 1 d . . .
C2 C 0.45982(13) 0.60473(17) 0.16307(9) 0.0387(4) Uani 1 1 d . . .
C3 C 0.56931(15) 0.6520(2) 0.13834(10) 0.0498(4) Uani 1 1 d . . .
H3 H 0.5958 0.5982 0.0924 0.060 Uiso 1 1 calc R . .
C4 C 0.63830(16) 0.7808(2) 0.18334(11) 0.0578(5) Uani 1 1 d . . .
H4 H 0.7129 0.8131 0.1684 0.069 Uiso 1 1 calc R . .
C5 C 0.59706(17) 0.8622(2) 0.25066(11) 0.0561(5) Uani 1 1 d . . .
H5 H 0.6450 0.9481 0.2808 0.067 Uiso 1 1 calc R . .
C6 C 0.48603(16) 0.8179(2) 0.27368(10) 0.0507(4) Uani 1 1 d . . .
H6 H 0.4577 0.8745 0.3179 0.061 Uiso 1 1 calc R . .
C7 C 0.41778(14) 0.68698(19) 0.22944(9) 0.0421(4) Uani 1 1 d . . .
C8 C 0.29627(16) 0.6126(2) 0.23886(11) 0.0516(4) Uani 1 1 d . . .
H8A H 0.3000 0.5854 0.3011 0.062 Uiso 1 1 calc R . .
H8B H 0.2259 0.6867 0.2174 0.062 Uiso 1 1 calc R . .
C9 C 0.40706(14) 0.30729(18) 0.10745(10) 0.0418(4) Uani 1 1 d . . .
C10 C 0.30966(14) 0.20377(17) 0.04902(9) 0.0414(4) Uani 1 1 d . . .
C11 C 0.19915(14) 0.27745(18) -0.00063(9) 0.0418(4) Uani 1 1 d . . .
C12 C 0.18017(15) 0.45831(19) 0.00259(11) 0.0469(4) Uani 1 1 d . . .
H12A H 0.1441 0.4980 -0.0577 0.056 Uiso 1 1 calc R . .
H12B H 0.1203 0.4815 0.0391 0.056 Uiso 1 1 calc R . .
C13 C 0.10833(16) 0.1797(2) -0.05383(12) 0.0567(4) Uani 1 1 d . . .
C14 C 0.1206(2) 0.0146(2) -0.06152(15) 0.0711(6) Uani 1 1 d . . .
H14 H 0.0574 -0.0471 -0.0986 0.085 Uiso 1 1 calc R . .
C15 C 0.2302(2) -0.0571(2) -0.01231(15) 0.0717(6) Uani 1 1 d . . .
H15 H 0.2413 -0.1692 -0.0163 0.086 Uiso 1 1 calc R . .
C16 C 0.32303(19) 0.0347(2) 0.04241(12) 0.0575(5) Uani 1 1 d . . .
H16 H 0.3958 -0.0162 0.0755 0.069 Uiso 1 1 calc R . .
C17 C 0.52403(19) 0.2587(2) 0.14251(16) 0.0749(6) Uani 1 1 d . . .
H17A H 0.5493 0.1541 0.1310 0.090 Uiso 1 1 calc R . .
H17B H 0.5813 0.3291 0.1788 0.090 Uiso 1 1 calc R . .
F1 F 0.00139(11) 0.25426(16) -0.10160(9) 0.0854(4) Uani 1 1 d . . .
O1 O 0.29532(9) 0.54259(11) 0.03864(7) 0.0415(3) Uani 1 1 d . . .
O2 O 0.28292(10) 0.46775(13) 0.18419(7) 0.0466(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 O2 1.4189(17) . ?
C1 O1 1.4342(17) . ?
C1 C2 1.502(2) . ?
C1 C9 1.5127(19) . ?
C2 C7 1.383(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.386(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.490(2) . ?
C8 O2 1.4401(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C17 1.318(2) . ?
C9 C10 1.480(2) . ?
C10 C11 1.397(2) . ?
C10 C16 1.400(2) . ?
C11 C13 1.378(2) . ?
C11 C12 1.499(2) . ?
C12 O1 1.4204(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 F1 1.362(2) . ?
C13 C14 1.367(3) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9300 . ?
C17 H17B 0.9300 . ?

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
O2 C1 O1 110.52(11) . . ?
O2 C1 C2 104.54(11) . . ?
O1 C1 C2 105.62(11) . . ?
O2 C1 C9 108.54(11) . . ?
O1 C1 C9 108.16(11) . . ?
C2 C1 C9 119.29(12) . . ?
C7 C2 C3 121.13(14) . . ?
C7 C2 C1 108.45(12) . . ?
C3 C2 C1 130.22(13) . . ?
C4 C3 C2 118.49(14) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 120.46(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 121.04(16) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.49(14) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 H6 120.8 . . ?
C2 C7 C6 120.37(14) . . ?
C2 C7 C8 108.89(13) . . ?
C6 C7 C8 130.73(13) . . ?
O2 C8 C7 104.57(11) . . ?
O2 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
O2 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C17 C9 C10 123.72(15) . . ?
C17 C9 C1 121.51(15) . . ?
C10 C9 C1 114.77(12) . . ?
C11 C10 C16 118.63(15) . . ?
C11 C10 C9 118.70(13) . . ?
C16 C10 C9 122.67(14) . . ?
C13 C11 C10 118.24(15) . . ?
C13 C11 C12 120.65(14) . . ?
C10 C11 C12 121.10(13) . . ?
O1 C12 C11 112.25(12) . . ?
O1 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
O1 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
F1 C13 C14 119.06(16) . . ?
F1 C13 C11 117.20(16) . . ?
C14 C13 C11 123.74(17) . . ?
C13 C14 C15 117.62(17) . . ?
C13 C14 H14 121.2 . . ?
C15 C14 H14 121.2 . . ?
C16 C15 C14 120.89(17) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C10 120.87(17) . . ?
C15 C16 H16 119.6 . . ?
C10 C16 H16 119.6 . . ?
C9 C17 H17A 120.0 . . ?
C9 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C12 O1 C1 112.82(11) . . ?
C1 O2 C8 109.94(10) . . ?

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
O2 C1 C2 C7 -13.39(15) . . . . ?
O1 C1 C2 C7 103.27(13) . . . . ?
C9 C1 C2 C7 -134.87(13) . . . . ?
O2 C1 C2 C3 171.89(15) . . . . ?
O1 C1 C2 C3 -71.45(19) . . . . ?
C9 C1 C2 C3 50.4(2) . . . . ?
C7 C2 C3 C4 1.9(2) . . . . ?
C1 C2 C3 C4 176.03(15) . . . . ?
C2 C3 C4 C5 -1.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C7 1.6(3) . . . . ?
C3 C2 C7 C6 -0.9(2) . . . . ?
C1 C2 C7 C6 -176.22(14) . . . . ?
C3 C2 C7 C8 177.96(14) . . . . ?
C1 C2 C7 C8 2.68(17) . . . . ?
C5 C6 C7 C2 -0.8(2) . . . . ?
C5 C6 C7 C8 -179.43(16) . . . . ?
C2 C7 C8 O2 8.90(17) . . . . ?
C6 C7 C8 O2 -172.35(16) . . . . ?
O2 C1 C9 C17 -106.53(19) . . . . ?
O1 C1 C9 C17 133.52(17) . . . . ?
C2 C1 C9 C17 12.9(2) . . . . ?
O2 C1 C9 C10 74.49(14) . . . . ?
O1 C1 C9 C10 -45.45(15) . . . . ?
C2 C1 C9 C10 -166.05(12) . . . . ?
C17 C9 C10 C11 -165.62(18) . . . . ?
C1 C9 C10 C11 13.33(18) . . . . ?
C17 C9 C10 C16 15.3(2) . . . . ?
C1 C9 C10 C16 -165.80(14) . . . . ?
C16 C10 C11 C13 0.0(2) . . . . ?
C9 C10 C11 C13 -179.12(13) . . . . ?
C16 C10 C11 C12 -179.09(14) . . . . ?
C9 C10 C11 C12 1.7(2) . . . . ?
C13 C11 C12 O1 -162.79(13) . . . . ?
C10 C11 C12 O1 16.3(2) . . . . ?
C10 C11 C13 F1 179.98(14) . . . . ?
C12 C11 C13 F1 -0.9(2) . . . . ?
C10 C11 C13 C14 -0.6(2) . . . . ?
C12 C11 C13 C14 178.50(17) . . . . ?
F1 C13 C14 C15 179.92(18) . . . . ?
C11 C13 C14 C15 0.6(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C10 -0.7(3) . . . . ?
C11 C10 C16 C15 0.6(2) . . . . ?
C9 C10 C16 C15 179.73(16) . . . . ?
C11 C12 O1 C1 -51.61(16) . . . . ?
O2 C1 O1 C12 -52.30(15) . . . . ?
C2 C1 O1 C12 -164.83(11) . . . . ?
C9 C1 O1 C12 66.39(14) . . . . ?
O1 C1 O2 C8 -93.85(14) . . . . ?
C2 C1 O2 C8 19.36(15) . . . . ?
C9 C1 O2 C8 147.69(13) . . . . ?
C7 C8 O2 C1 -17.86(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.035
