# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_wl130423

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H10 F2 O2'
_chemical_formula_weight         212.19

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                   4.8650(10)
_cell_length_b                   7.0570(14)
_cell_length_c                   15.151(3)
_cell_angle_alpha                88.73(3)
_cell_angle_beta                 84.04(3)
_cell_angle_gamma                82.71(3)
_cell_volume                     513.15(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    460
_cell_measurement_theta_min      3.1915
_cell_measurement_theta_max      28.7523

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38159
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2864
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1806
_reflns_number_gt                759
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP-III
_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)+(0.0994P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1806
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1590
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.1644
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
F1 F 0.6373(6) 0.0674(4) 0.19717(17) 0.1017(11) Uani 1 1 d . . .
F2 F 0.2579(6) 0.2611(4) 0.10623(18) 0.1068(11) Uani 1 1 d . . .
O1 O 1.2932(6) 0.2252(5) 0.5146(2) 0.0924(12) Uani 1 1 d . . .
H1 H 1.4191 0.1506 0.5324 0.139 Uiso 1 1 calc R . .
O2 O 1.2938(6) -0.0098(5) 0.41737(19) 0.0812(11) Uani 1 1 d . . .
C1 C 1.2007(9) 0.1513(7) 0.4473(3) 0.0723(14) Uani 1 1 d . . .
C2 C 0.9742(8) 0.2712(7) 0.4089(3) 0.0762(14) Uani 1 1 d . . .
H2 H 0.9078 0.3895 0.4339 0.091 Uiso 1 1 calc R . .
C3 C 0.8610(8) 0.2154(7) 0.3393(3) 0.0711(13) Uani 1 1 d . . .
H3 H 0.9254 0.0934 0.3182 0.085 Uiso 1 1 calc R . .
C4 C 0.6449(8) 0.3268(6) 0.2924(3) 0.0660(12) Uani 1 1 d . . .
C5 C 0.5448(8) 0.2469(7) 0.2215(3) 0.0707(13) Uani 1 1 d . . .
C6 C 0.3473(9) 0.3513(7) 0.1740(3) 0.0753(14) Uani 1 1 d . . .
C7 C 0.2400(9) 0.5344(7) 0.1939(3) 0.0732(13) Uani 1 1 d . . .
C8 C 0.3345(9) 0.6131(7) 0.2668(3) 0.0844(16) Uani 1 1 d . . .
H8 H 0.2624 0.7367 0.2839 0.101 Uiso 1 1 calc R . .
C9 C 0.5324(9) 0.5121(7) 0.3142(3) 0.0818(15) Uani 1 1 d . . .
H9 H 0.5920 0.5698 0.3621 0.098 Uiso 1 1 calc R . .
C10 C 0.0375(10) 0.6468(8) 0.1372(4) 0.1006(19) Uani 1 1 d . . .
H10A H -0.0762 0.5606 0.1135 0.121 Uiso 1 1 calc R . .
H10B H -0.0853 0.7394 0.1739 0.121 Uiso 1 1 calc R . .
C11 C 0.1820(13) 0.7484(9) 0.0624(4) 0.133(2) Uani 1 1 d . . .
H11A H 0.2880 0.8382 0.0856 0.200 Uiso 1 1 calc R . .
H11B H 0.0465 0.8150 0.0273 0.200 Uiso 1 1 calc R . .
H11C H 0.3047 0.6573 0.0261 0.200 Uiso 1 1 calc R . .

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
F1 0.125(2) 0.077(2) 0.104(2) -0.0186(16) -0.0576(18) 0.0232(17)
F2 0.130(2) 0.101(2) 0.0959(19) -0.0160(17) -0.0684(18) 0.0087(17)
O1 0.104(2) 0.092(3) 0.084(2) -0.0086(18) -0.0534(19) 0.0170(18)
O2 0.094(2) 0.075(2) 0.076(2) -0.0051(17) -0.0412(17) 0.0143(18)
C1 0.077(3) 0.080(4) 0.060(3) 0.006(3) -0.028(2) 0.005(3)
C2 0.075(3) 0.081(3) 0.072(3) 0.002(2) -0.028(3) 0.008(2)
C3 0.071(3) 0.074(3) 0.070(3) 0.000(2) -0.030(2) 0.004(2)
C4 0.070(3) 0.067(3) 0.063(3) 0.002(2) -0.029(2) 0.003(2)
C5 0.076(3) 0.065(3) 0.070(3) -0.004(2) -0.025(2) 0.010(2)
C6 0.084(3) 0.085(4) 0.061(3) -0.002(2) -0.034(2) -0.002(3)
C7 0.073(3) 0.069(3) 0.077(3) 0.005(2) -0.026(2) 0.009(2)
C8 0.097(3) 0.070(3) 0.086(3) -0.007(3) -0.037(3) 0.018(3)
C9 0.096(3) 0.071(3) 0.079(3) -0.014(3) -0.037(3) 0.015(3)
C10 0.103(4) 0.089(4) 0.111(4) 0.017(3) -0.053(4) 0.015(3)
C11 0.161(6) 0.122(6) 0.124(5) 0.046(4) -0.067(5) -0.011(5)

_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 C5 1.336(4) . ?
F2 C6 1.357(4) . ?
O1 C1 1.300(5) . ?
O1 H1 0.8200 . ?
O2 C1 1.246(5) . ?
C1 C2 1.464(6) . ?
C2 C3 1.329(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.466(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(5) . ?
C4 C9 1.385(5) . ?
C5 C6 1.387(5) . ?
C6 C7 1.359(6) . ?
C7 C8 1.392(6) . ?
C7 C10 1.511(6) . ?
C8 C9 1.377(5) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.490(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
C1 O1 H1 109.5 . . ?
O2 C1 O1 123.4(4) . . ?
O2 C1 C2 121.7(4) . . ?
O1 C1 C2 114.9(4) . . ?
C3 C2 C1 121.7(4) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 126.6(4) . . ?
C2 C3 H3 116.7 . . ?
C4 C3 H3 116.7 . . ?
C5 C4 C9 116.6(4) . . ?
C5 C4 C3 119.6(4) . . ?
C9 C4 C3 123.8(4) . . ?
F1 C5 C4 120.6(4) . . ?
F1 C5 C6 118.6(4) . . ?
C4 C5 C6 120.8(4) . . ?
F2 C6 C7 120.1(4) . . ?
F2 C6 C5 117.0(4) . . ?
C7 C6 C5 122.9(4) . . ?
C6 C7 C8 116.3(4) . . ?
C6 C7 C10 121.2(4) . . ?
C8 C7 C10 122.5(4) . . ?
C9 C8 C7 121.5(4) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C4 121.8(4) . . ?
C8 C9 H9 119.1 . . ?
C4 C9 H9 119.1 . . ?
C11 C10 C7 112.2(4) . . ?
C11 C10 H10A 109.2 . . ?
C7 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C7 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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 C3 -1.3(8) . . . . ?
O1 C1 C2 C3 179.2(4) . . . . ?
C1 C2 C3 C4 -176.5(4) . . . . ?
C2 C3 C4 C5 -178.9(4) . . . . ?
C2 C3 C4 C9 1.6(8) . . . . ?
C9 C4 C5 F1 -178.5(4) . . . . ?
C3 C4 C5 F1 2.0(7) . . . . ?
C9 C4 C5 C6 1.7(7) . . . . ?
C3 C4 C5 C6 -177.8(4) . . . . ?
F1 C5 C6 F2 1.1(7) . . . . ?
C4 C5 C6 F2 -179.1(4) . . . . ?
F1 C5 C6 C7 179.8(4) . . . . ?
C4 C5 C6 C7 -0.5(8) . . . . ?
F2 C6 C7 C8 177.3(4) . . . . ?
C5 C6 C7 C8 -1.4(8) . . . . ?
F2 C6 C7 C10 -4.9(7) . . . . ?
C5 C6 C7 C10 176.5(5) . . . . ?
C6 C7 C8 C9 1.9(8) . . . . ?
C10 C7 C8 C9 -175.8(5) . . . . ?
C7 C8 C9 C4 -0.7(8) . . . . ?
C5 C4 C9 C8 -1.1(7) . . . . ?
C3 C4 C9 C8 178.3(5) . . . . ?
C6 C7 C10 C11 -88.0(6) . . . . ?
C8 C7 C10 C11 89.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 953222'
