# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_ds1202

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          381.15-383.15
_chemical_formula_moiety         'C22 H19 F O2'
_chemical_formula_sum            'C22 H19 F O2'
_chemical_formula_weight         334.37

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)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5436(6)
_cell_length_b                   8.7069(3)
_cell_length_c                   12.5382(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.769(1)
_cell_angle_gamma                90.00
_cell_volume                     1694.9(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    4242
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            9843
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3836
_reflns_number_gt                2274
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0542P)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         3836
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0945
_refine_ls_goodness_of_fit_ref   0.906
_refine_ls_restrained_S_all      0.906
_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 0.94923(10) 0.1585(2) 0.72038(13) 0.0565(4) Uani 1 1 d . . .
H1A H 1.0032 0.2098 0.7269 0.068 Uiso 1 1 calc R . .
O1 O 0.58473(7) 0.24923(11) 0.63896(7) 0.0500(3) Uani 1 1 d . . .
O2 O 0.55648(6) 0.01776(11) 0.70753(7) 0.0436(3) Uani 1 1 d . . .
F1 F 0.94629(6) 0.19890(13) 0.53617(7) 0.0754(3) Uani 1 1 d . . .
C2 C 0.91138(10) 0.10039(19) 0.80849(12) 0.0516(4) Uani 1 1 d . . .
H2 H 0.9392 0.1107 0.8773 0.062 Uiso 1 1 calc R . .
C3 C 0.83346(10) 0.02762(19) 0.79677(11) 0.0484(4) Uani 1 1 d . . .
H3 H 0.8071 -0.0123 0.8577 0.058 Uiso 1 1 calc R . .
C4 C 0.79279(9) 0.01187(17) 0.69680(10) 0.0427(4) Uani 1 1 d . . .
H4 H 0.7393 -0.0408 0.6904 0.051 Uiso 1 1 calc R . .
C5 C 0.90685(9) 0.14021(18) 0.62241(11) 0.0444(4) Uani 1 1 d . . .
C6 C 0.82782(9) 0.07083(15) 0.60533(10) 0.0332(3) Uani 1 1 d . . .
C7 C 0.78570(9) 0.06262(15) 0.49396(10) 0.0354(3) Uani 1 1 d . . .
H7 H 0.8184 0.1367 0.4503 0.043 Uiso 1 1 calc R . .
C8 C 0.79137(9) -0.09587(15) 0.43452(10) 0.0365(3) Uani 1 1 d . . .
H8 H 0.8403 -0.0950 0.3856 0.044 Uiso 1 1 calc R . .
C9 C 0.68947(9) 0.11015(15) 0.47742(10) 0.0357(3) Uani 1 1 d . . .
H9 H 0.6825 0.2239 0.4842 0.043 Uiso 1 1 calc R . .
C10 C 0.70435(9) -0.10738(16) 0.36900(10) 0.0393(4) Uani 1 1 d . . .
H10 H 0.7116 -0.1528 0.2968 0.047 Uiso 1 1 calc R . .
C11 C 0.67148(10) 0.05784(16) 0.36179(10) 0.0419(4) Uani 1 1 d . . .
H11A H 0.6093 0.0620 0.3410 0.050 Uiso 1 1 calc R . .
H11B H 0.7040 0.1196 0.3111 0.050 Uiso 1 1 calc R . .
C12 C 0.62676(8) 0.02548(15) 0.54544(10) 0.0338(3) Uani 1 1 d . . .
C13 C 0.64766(8) -0.21007(15) 0.43821(10) 0.0366(3) Uani 1 1 d . . .
H13 H 0.6056 -0.2723 0.3935 0.044 Uiso 1 1 calc R . .
C14 C 0.60421(9) -0.11889(16) 0.52180(10) 0.0358(3) Uani 1 1 d . . .
H14 H 0.5592 -0.1654 0.5591 0.043 Uiso 1 1 calc R . .
C15 C 0.58802(8) 0.11106(16) 0.63272(10) 0.0359(3) Uani 1 1 d . . .
C16 C 0.51922(10) 0.09281(18) 0.79730(11) 0.0495(4) Uani 1 1 d . . .
H16A H 0.4894 0.0166 0.8396 0.074 Uiso 1 1 calc R . .
H16B H 0.4781 0.1711 0.7712 0.074 Uiso 1 1 calc R . .
H16C H 0.5650 0.1416 0.8419 0.074 Uiso 1 1 calc R . .
C17 C 0.79385(9) -0.24024(15) 0.50095(10) 0.0340(3) Uani 1 1 d . . .
C18 C 0.71368(9) -0.31079(15) 0.49841(10) 0.0336(3) Uani 1 1 d . . .
C19 C 0.70152(9) -0.44913(15) 0.54976(10) 0.0372(3) Uani 1 1 d . . .
H19 H 0.6463 -0.4963 0.5482 0.045 Uiso 1 1 calc R . .
C20 C 0.77150(10) -0.51764(16) 0.60357(11) 0.0415(4) Uani 1 1 d . . .
H20 H 0.7646 -0.6136 0.6382 0.050 Uiso 1 1 calc R . .
C21 C 0.85133(10) -0.44719(17) 0.60707(11) 0.0432(4) Uani 1 1 d . . .
H21 H 0.8986 -0.4949 0.6448 0.052 Uiso 1 1 calc R . .
C22 C 0.86339(9) -0.30774(16) 0.55625(10) 0.0405(4) Uani 1 1 d . . .
H22 H 0.9183 -0.2595 0.5593 0.049 Uiso 1 1 calc R . .


_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 1.373(2) . ?
C1 C5 1.375(2) . ?
C1 H1A 0.9500 . ?
O1 C15 1.2068(16) . ?
O2 C15 1.3508(16) . ?
O2 C16 1.4465(16) . ?
F1 C5 1.3676(15) . ?
C2 C3 1.368(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.3831(19) . ?
C3 H3 0.9500 . ?
C4 C6 1.3912(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3763(19) . ?
C6 C7 1.5150(18) . ?
C7 C9 1.5561(19) . ?
C7 C8 1.5728(19) . ?
C7 H7 1.0000 . ?
C8 C17 1.5073(19) . ?
C8 C10 1.552(2) . ?
C8 H8 1.0000 . ?
C9 C12 1.5170(17) . ?
C9 C11 1.5324(18) . ?
C9 H9 1.0000 . ?
C10 C11 1.5278(19) . ?
C10 C13 1.5500(19) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C14 1.3344(18) . ?
C12 C15 1.4762(18) . ?
C13 C14 1.5012(18) . ?
C13 C18 1.5222(19) . ?
C13 H13 1.0000 . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C22 1.3864(19) . ?
C17 C18 1.3882(18) . ?
C18 C19 1.3831(18) . ?
C19 C20 1.387(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.388(2) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?

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 C5 118.08(14) . . ?
C2 C1 H1A 121.0 . . ?
C5 C1 H1A 121.0 . . ?
C15 O2 C16 116.17(11) . . ?
C3 C2 C1 119.71(14) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.44(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C6 122.04(13) . . ?
C3 C4 H4 119.0 . . ?
C6 C4 H4 119.0 . . ?
F1 C5 C1 116.71(13) . . ?
F1 C5 C6 118.15(12) . . ?
C1 C5 C6 125.12(13) . . ?
C5 C6 C4 114.56(12) . . ?
C5 C6 C7 120.45(11) . . ?
C4 C6 C7 124.99(12) . . ?
C6 C7 C9 118.69(10) . . ?
C6 C7 C8 116.52(10) . . ?
C9 C7 C8 104.22(10) . . ?
C6 C7 H7 105.4 . . ?
C9 C7 H7 105.4 . . ?
C8 C7 H7 105.4 . . ?
C17 C8 C10 103.71(11) . . ?
C17 C8 C7 118.06(10) . . ?
C10 C8 C7 103.90(10) . . ?
C17 C8 H8 110.2 . . ?
C10 C8 H8 110.2 . . ?
C7 C8 H8 110.2 . . ?
C12 C9 C11 107.13(11) . . ?
C12 C9 C7 115.81(10) . . ?
C11 C9 C7 100.22(10) . . ?
C12 C9 H9 111.0 . . ?
C11 C9 H9 111.0 . . ?
C7 C9 H9 111.0 . . ?
C11 C10 C13 112.26(11) . . ?
C11 C10 C8 104.54(11) . . ?
C13 C10 C8 104.21(10) . . ?
C11 C10 H10 111.8 . . ?
C13 C10 H10 111.8 . . ?
C8 C10 H10 111.8 . . ?
C10 C11 C9 100.29(10) . . ?
C10 C11 H11A 111.7 . . ?
C9 C11 H11A 111.7 . . ?
C10 C11 H11B 111.7 . . ?
C9 C11 H11B 111.7 . . ?
H11A C11 H11B 109.5 . . ?
C14 C12 C15 121.86(12) . . ?
C14 C12 C9 120.13(12) . . ?
C15 C12 C9 117.88(11) . . ?
C14 C13 C18 105.89(10) . . ?
C14 C13 C10 111.89(11) . . ?
C18 C13 C10 102.83(10) . . ?
C14 C13 H13 111.9 . . ?
C18 C13 H13 111.9 . . ?
C10 C13 H13 111.9 . . ?
C12 C14 C13 122.07(13) . . ?
C12 C14 H14 119.0 . . ?
C13 C14 H14 119.0 . . ?
O1 C15 O2 122.45(12) . . ?
O1 C15 C12 124.84(12) . . ?
O2 C15 C12 112.70(12) . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 120.08(13) . . ?
C22 C17 C8 128.93(12) . . ?
C18 C17 C8 110.94(12) . . ?
C19 C18 C17 121.16(13) . . ?
C19 C18 C13 128.94(12) . . ?
C17 C18 C13 109.84(11) . . ?
C18 C19 C20 118.65(13) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C21 C20 C19 120.41(13) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.94(14) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C21 118.75(13) . . ?
C17 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.037
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexanes, ethyl acetate '
_database_code_depnum_ccdc_archive 'CCDC 936207'
