# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_s
_database_code_depnum_ccdc_archive 'CCDC 1583436'
_audit_update_record             
;
2017-11-06 deposited with the CCDC.
2018-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H10 F2 O3'
_chemical_formula_weight         288.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables 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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.0746(17)
_cell_length_b                   8.499(2)
_cell_length_c                   10.459(2)
_cell_angle_alpha                92.779(6)
_cell_angle_beta                 104.832(6)
_cell_angle_gamma                93.958(6)
_cell_volume                     605.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    9268
_cell_measurement_theta_min      5.229
_cell_measurement_theta_max      68.314

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    1.108
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.6072
_exptl_absorpt_correction_T_max  0.7321
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14458
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.23
_diffrn_reflns_theta_max         68.31
_reflns_number_total             2204
_reflns_number_gt                2180
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0633P)²+0.1768P] 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       0.076(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2204
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.59208(18) 0.26788(14) 0.31130(12) 0.0212(3) Uani 1 1 d . . .
C2 C 0.66864(19) 0.17850(15) 0.41131(13) 0.0234(3) Uani 1 1 d . . .
C3 C 0.77532(18) 0.23765(15) 0.54414(13) 0.0222(3) Uani 1 1 d . . .
C4 C 0.89861(17) 0.49826(15) 0.68094(12) 0.0214(3) Uani 1 1 d . . .
C5 C 0.91342(18) 0.66090(16) 0.68449(13) 0.0229(3) Uani 1 1 d . . .
C6 C 0.83212(18) 0.74527(15) 0.57691(13) 0.0242(3) Uani 1 1 d . . .
H6 H 0.8448 0.8576 0.5838 0.029 Uiso 1 1 calc R . .
C7 C 0.73230(18) 0.66297(15) 0.45941(13) 0.0233(3) Uani 1 1 d . . .
H7 H 0.6754 0.7178 0.3839 0.028 Uiso 1 1 calc R . .
C8 C 0.71603(18) 0.49858(15) 0.45305(13) 0.0206(3) Uani 1 1 d . . .
C9 C 0.79593(17) 0.41175(15) 0.56130(13) 0.0207(3) Uani 1 1 d . . .
C10 C 0.50157(19) 0.30559(15) 0.07057(13) 0.0256(3) Uani 1 1 d . . .
H10 H 0.5894 0.3985 0.0875 0.031 Uiso 1 1 calc R . .
C11 C 0.3931(2) 0.26014(17) -0.05741(13) 0.0298(3) Uani 1 1 d . . .
H11 H 0.4058 0.3228 -0.1280 0.036 Uiso 1 1 calc R . .
C12 C 0.2660(2) 0.12377(17) -0.08355(14) 0.0299(3) Uani 1 1 d . . .
H12 H 0.1909 0.0936 -0.1715 0.036 Uiso 1 1 calc R . .
C13 C 0.24923(19) 0.03191(16) 0.01965(14) 0.0284(3) Uani 1 1 d . . .
H13 H 0.1645 -0.0627 0.0018 0.034 Uiso 1 1 calc R . .
C14 C 0.35516(19) 0.07708(16) 0.14882(13) 0.0256(3) Uani 1 1 d . . .
H14 H 0.3414 0.0144 0.2192 0.031 Uiso 1 1 calc R . .
C15 C 0.48183(18) 0.21467(15) 0.17507(12) 0.0219(3) Uani 1 1 d . . .
C16 C 0.8620(2) 0.37407(18) 0.86936(14) 0.0341(4) Uani 1 1 d . . .
H16A H 0.7634 0.2932 0.8170 0.051 Uiso 1 1 calc R . .
H16B H 0.7963 0.4636 0.8951 0.051 Uiso 1 1 calc R . .
H16C H 0.9380 0.3292 0.9491 0.051 Uiso 1 1 calc R . .
F1 F 0.65036(13) 0.01984(9) 0.38951(8) 0.0338(3) Uani 1 1 d . . .
F2 F 1.01459(12) 0.74175(9) 0.79877(8) 0.0304(3) Uani 1 1 d . . .
O1 O 0.61583(13) 0.42824(10) 0.33141(9) 0.0228(3) Uani 1 1 d . . .
O2 O 0.84024(15) 0.14788(11) 0.63017(9) 0.0309(3) Uani 1 1 d . . .
O3 O 0.99138(13) 0.42728(11) 0.79133(9) 0.0271(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0211(6) 0.0186(6) 0.0251(7) 0.0019(5) 0.0083(5) 0.0023(5)
C2 0.0266(6) 0.0175(6) 0.0267(7) 0.0018(5) 0.0077(5) 0.0023(5)
C3 0.0228(6) 0.0222(6) 0.0236(6) 0.0043(5) 0.0088(5) 0.0038(5)
C4 0.0185(6) 0.0249(7) 0.0221(6) 0.0036(5) 0.0071(5) 0.0037(5)
C5 0.0207(6) 0.0256(7) 0.0220(6) -0.0022(5) 0.0058(5) 0.0014(5)
C6 0.0247(6) 0.0200(6) 0.0290(7) 0.0008(5) 0.0092(5) 0.0021(5)
C7 0.0245(6) 0.0213(7) 0.0250(7) 0.0045(5) 0.0068(5) 0.0048(5)
C8 0.0190(6) 0.0226(6) 0.0206(6) 0.0008(5) 0.0062(5) 0.0017(5)
C9 0.0190(6) 0.0221(7) 0.0231(6) 0.0036(5) 0.0082(5) 0.0033(5)
C10 0.0277(7) 0.0219(6) 0.0272(7) 0.0027(5) 0.0065(5) 0.0028(5)
C11 0.0358(7) 0.0301(7) 0.0234(7) 0.0046(5) 0.0060(5) 0.0069(6)
C12 0.0286(7) 0.0319(7) 0.0260(7) -0.0031(5) 0.0009(5) 0.0075(5)
C13 0.0235(6) 0.0261(7) 0.0333(7) -0.0035(5) 0.0046(5) 0.0008(5)
C14 0.0246(6) 0.0248(7) 0.0278(7) 0.0026(5) 0.0072(5) 0.0028(5)
C15 0.0214(6) 0.0212(6) 0.0235(6) 0.0009(5) 0.0055(5) 0.0058(5)
C16 0.0451(8) 0.0338(8) 0.0261(7) 0.0071(6) 0.0134(6) 0.0030(6)
F1 0.0491(5) 0.0169(4) 0.0309(5) 0.0020(3) 0.0018(4) 0.0045(3)
F2 0.0343(5) 0.0283(4) 0.0244(4) -0.0050(3) 0.0017(3) 0.0007(3)
O1 0.0269(5) 0.0187(5) 0.0211(5) 0.0017(3) 0.0030(4) 0.0022(4)
O2 0.0433(6) 0.0229(5) 0.0253(5) 0.0073(4) 0.0047(4) 0.0065(4)
O3 0.0276(5) 0.0309(5) 0.0215(5) 0.0069(4) 0.0031(4) 0.0037(4)

_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 C2 1.3447(19) . ?
C1 O1 1.3610(15) . ?
C1 C15 1.4706(18) . ?
C2 F1 1.3483(15) . ?
C2 C3 1.4475(19) . ?
C3 O2 1.2272(16) . ?
C3 C9 1.4745(18) . ?
C4 O3 1.3645(16) . ?
C4 C5 1.3770(19) . ?
C4 C9 1.4162(19) . ?
C5 F2 1.3519(15) . ?
C5 C6 1.3837(19) . ?
C6 C7 1.3792(19) . ?
C7 C8 1.3908(19) . ?
C8 O1 1.3727(15) . ?
C8 C9 1.3989(18) . ?
C10 C11 1.3829(19) . ?
C10 C15 1.3987(19) . ?
C11 C12 1.388(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.3876(19) . ?
C14 C15 1.3943(19) . ?
C16 O3 1.4387(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 119.52(12) . . ?
C2 C1 C15 127.96(12) . . ?
O1 C1 C15 112.51(10) . . ?
C1 C2 F1 119.24(12) . . ?
C1 C2 C3 125.55(12) . . ?
F1 C2 C3 115.20(11) . . ?
O2 C3 C2 121.54(12) . . ?
O2 C3 C9 125.56(12) . . ?
C2 C3 C9 112.90(11) . . ?
O3 C4 C5 118.41(12) . . ?
O3 C4 C9 122.75(12) . . ?
C5 C4 C9 118.77(12) . . ?
F2 C5 C4 118.06(11) . . ?
F2 C5 C6 118.54(12) . . ?
C4 C5 C6 123.39(12) . . ?
C7 C6 C5 118.64(12) . . ?
C6 C7 C8 119.10(12) . . ?
O1 C8 C7 114.47(11) . . ?
O1 C8 C9 122.64(11) . . ?
C7 C8 C9 122.89(12) . . ?
C8 C9 C4 117.21(12) . . ?
C8 C9 C3 118.99(12) . . ?
C4 C9 C3 123.76(12) . . ?
C11 C10 C15 119.92(12) . . ?
C10 C11 C12 120.56(13) . . ?
C13 C12 C11 119.54(12) . . ?
C12 C13 C14 120.55(12) . . ?
C13 C14 C15 119.84(12) . . ?
C14 C15 C10 119.56(12) . . ?
C14 C15 C1 121.11(11) . . ?
C10 C15 C1 119.31(11) . . ?
C1 O1 C8 120.38(10) . . ?
C4 O3 C16 113.38(10) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        68.31
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.087
