# 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.
#
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#  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_rovis169_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F3 O2'
_chemical_formula_weight         256.22

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                   7.6763(3)
_cell_length_b                   10.0446(4)
_cell_length_c                   15.7356(6)
_cell_angle_alpha                81.300(2)
_cell_angle_beta                 82.163(2)
_cell_angle_gamma                86.148(2)
_cell_volume                     1186.79(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8831
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      28.21

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9937
_exptl_absorpt_process_details   
'Sheldrick, G. M. (2008) SADABS. University of Göttingen, Germany.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      120(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 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20906
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         28.32
_reflns_number_total             5867
_reflns_number_gt                3879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'APEX2 (Bruker, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0373P)²+0.1890P] 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         5867
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_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 -0.21599(18) 0.47284(13) 0.95940(9) 0.0228(3) Uani 1 1 d . . .
C2 C -0.14539(19) 0.34165(13) 0.97113(10) 0.0249(3) Uani 1 1 d . . .
H2 H -0.1630 0.2879 1.0264 0.030 Uiso 1 1 calc R . .
C3 C -0.04906(19) 0.28947(13) 0.90170(9) 0.0242(3) Uani 1 1 d . . .
H3 H -0.0015 0.1994 0.9103 0.029 Uiso 1 1 calc R . .
C4 C -0.01970(18) 0.36478(13) 0.81979(9) 0.0218(3) Uani 1 1 d . . .
C5 C -0.09559(19) 0.49659(13) 0.80892(10) 0.0253(3) Uani 1 1 d . . .
H5 H -0.0801 0.5499 0.7534 0.030 Uiso 1 1 calc R . .
C6 C -0.19150(19) 0.54945(13) 0.87707(10) 0.0264(3) Uani 1 1 d . . .
H6 H -0.2417 0.6387 0.8683 0.032 Uiso 1 1 calc R . .
C7 C 0.08570(19) 0.30590(13) 0.74911(10) 0.0251(3) Uani 1 1 d . . .
H7 H 0.1278 0.2150 0.7622 0.030 Uiso 1 1 calc R . .
C8 C 0.12949(19) 0.36651(14) 0.66769(10) 0.0257(3) Uani 1 1 d . . .
H8 H 0.0921 0.4583 0.6532 0.031 Uiso 1 1 calc R . .
C9 C 0.22984(19) 0.29962(14) 0.60164(10) 0.0247(3) Uani 1 1 d . . .
H9 H 0.2667 0.2079 0.6168 0.030 Uiso 1 1 calc R . .
C10 C 0.27533(19) 0.35780(14) 0.51978(10) 0.0267(3) Uani 1 1 d . . .
H10 H 0.2460 0.4509 0.5042 0.032 Uiso 1 1 calc R . .
C11 C 0.36818(19) 0.28223(13) 0.45447(10) 0.0246(3) Uani 1 1 d . . .
C12 C 0.4404(2) 0.36379(14) 0.36759(10) 0.0276(4) Uani 1 1 d . . .
C13 C -0.3352(2) 0.46106(15) 1.10796(10) 0.0338(4) Uani 1 1 d . . .
H13A H -0.4022 0.3816 1.1074 0.051 Uiso 1 1 calc R . .
H13B H -0.4000 0.5180 1.1482 0.051 Uiso 1 1 calc R . .
H13C H -0.2203 0.4323 1.1267 0.051 Uiso 1 1 calc R . .
C14 C 0.66916(18) 0.94825(13) 0.07979(9) 0.0210(3) Uani 1 1 d . . .
C15 C 0.65475(19) 1.02231(13) 0.14909(9) 0.0226(3) Uani 1 1 d . . .
H15 H 0.7217 1.0999 0.1442 0.027 Uiso 1 1 calc R . .
C16 C 0.54496(19) 0.98413(13) 0.22402(9) 0.0227(3) Uani 1 1 d . . .
H16 H 0.5366 1.0358 0.2703 0.027 Uiso 1 1 calc R . .
C17 C 0.44477(18) 0.86974(13) 0.23318(9) 0.0210(3) Uani 1 1 d . . .
C18 C 0.45950(19) 0.79873(13) 0.16254(9) 0.0231(3) Uani 1 1 d . . .
H18 H 0.3914 0.7219 0.1669 0.028 Uiso 1 1 calc R . .
C19 C 0.56927(19) 0.83588(13) 0.08669(10) 0.0236(3) Uani 1 1 d . . .
H19 H 0.5764 0.7853 0.0399 0.028 Uiso 1 1 calc R . .
C20 C 0.33045(19) 0.82322(13) 0.31174(9) 0.0232(3) Uani 1 1 d . . .
H20 H 0.2646 0.7470 0.3103 0.028 Uiso 1 1 calc R . .
C21 C 0.30702(19) 0.87575(14) 0.38650(9) 0.0247(3) Uani 1 1 d . . .
H21 H 0.3695 0.9527 0.3902 0.030 Uiso 1 1 calc R . .
C22 C 0.19197(19) 0.82016(13) 0.46025(9) 0.0238(3) Uani 1 1 d . . .
H22 H 0.1304 0.7433 0.4553 0.029 Uiso 1 1 calc R . .
C23 C 0.16416(19) 0.86879(14) 0.53662(9) 0.0252(3) Uani 1 1 d . . .
H23 H 0.2205 0.9474 0.5430 0.030 Uiso 1 1 calc R . .
C24 C 0.04978(19) 0.80247(13) 0.60849(9) 0.0220(3) Uani 1 1 d . . .
C25 C 0.0310(2) 0.85974(13) 0.69474(10) 0.0258(3) Uani 1 1 d . . .
C26 C 0.8049(2) 0.92217(14) -0.06301(9) 0.0284(4) Uani 1 1 d . . .
H26A H 0.8400 0.8277 -0.0448 0.043 Uiso 1 1 calc R . .
H26B H 0.8951 0.9629 -0.1077 0.043 Uiso 1 1 calc R . .
H26C H 0.6924 0.9269 -0.0865 0.043 Uiso 1 1 calc R . .
F1 F 0.44394(13) 0.29428(9) 0.30168(6) 0.0435(3) Uani 1 1 d . . .
F2 F 0.60592(12) 0.39505(9) 0.37052(6) 0.0434(3) Uani 1 1 d . . .
F3 F 0.34942(12) 0.47941(8) 0.34744(6) 0.0389(2) Uani 1 1 d . . .
F4 F 0.13805(13) 0.78821(9) 0.74714(6) 0.0406(3) Uani 1 1 d . . .
F5 F -0.13163(12) 0.85109(9) 0.73599(6) 0.0401(2) Uani 1 1 d . . .
F6 F 0.07228(12) 0.98837(8) 0.68643(6) 0.0361(2) Uani 1 1 d . . .
O1 O 0.39942(14) 0.16105(9) 0.46310(7) 0.0325(3) Uani 1 1 d . . .
O2 O -0.31056(13) 0.53581(9) 1.02289(7) 0.0297(3) Uani 1 1 d . . .
O3 O -0.02992(13) 0.70129(10) 0.60927(6) 0.0284(3) Uani 1 1 d . . .
O4 O 0.78616(13) 0.99367(9) 0.00998(6) 0.0256(2) 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 1.3627(17) . ?
C1 C2 1.3864(18) . ?
C1 C6 1.399(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.4059(18) . ?
C4 C7 1.460(2) . ?
C5 C6 1.371(2) . ?
C7 C8 1.341(2) . ?
C8 C9 1.431(2) . ?
C9 C10 1.342(2) . ?
C10 C11 1.451(2) . ?
C11 O1 1.2154(15) . ?
C11 C12 1.537(2) . ?
C12 F1 1.3315(17) . ?
C12 F3 1.3330(15) . ?
C12 F2 1.3375(17) . ?
C13 O2 1.4273(18) . ?
C14 O4 1.3623(17) . ?
C14 C19 1.389(2) . ?
C14 C15 1.3986(19) . ?
C15 C16 1.372(2) . ?
C16 C17 1.4039(19) . ?
C17 C18 1.3970(19) . ?
C17 C20 1.450(2) . ?
C18 C19 1.381(2) . ?
C20 C21 1.3460(19) . ?
C21 C22 1.424(2) . ?
C22 C23 1.350(2) . ?
C23 C24 1.440(2) . ?
C24 O3 1.2186(16) . ?
C24 C25 1.538(2) . ?
C25 F5 1.3283(17) . ?
C25 F6 1.3340(15) . ?
C25 F4 1.3407(16) . ?
C26 O4 1.4305(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
O2 C1 C2 124.91(13) . . ?
O2 C1 C6 115.73(12) . . ?
C2 C1 C6 119.37(13) . . ?
C3 C2 C1 119.55(13) . . ?
C2 C3 C4 122.06(12) . . ?
C3 C4 C5 117.43(13) . . ?
C3 C4 C7 119.92(12) . . ?
C5 C4 C7 122.65(13) . . ?
C6 C5 C4 121.10(14) . . ?
C5 C6 C1 120.47(13) . . ?
C8 C7 C4 126.93(13) . . ?
C7 C8 C9 123.16(13) . . ?
C10 C9 C8 124.36(13) . . ?
C9 C10 C11 121.69(13) . . ?
O1 C11 C10 126.07(14) . . ?
O1 C11 C12 116.99(13) . . ?
C10 C11 C12 116.89(12) . . ?
F1 C12 F3 106.94(12) . . ?
F1 C12 F2 107.15(12) . . ?
F3 C12 F2 106.93(12) . . ?
F1 C12 C11 112.06(12) . . ?
F3 C12 C11 113.87(12) . . ?
F2 C12 C11 109.54(12) . . ?
O4 C14 C19 125.21(13) . . ?
O4 C14 C15 115.31(12) . . ?
C19 C14 C15 119.47(14) . . ?
C16 C15 C14 120.73(13) . . ?
C15 C16 C17 120.93(13) . . ?
C18 C17 C16 117.21(13) . . ?
C18 C17 C20 119.73(13) . . ?
C16 C17 C20 123.05(13) . . ?
C19 C18 C17 122.56(13) . . ?
C18 C19 C14 119.09(13) . . ?
C21 C20 C17 127.39(14) . . ?
C20 C21 C22 122.42(14) . . ?
C23 C22 C21 124.72(14) . . ?
C22 C23 C24 120.54(14) . . ?
O3 C24 C23 126.53(14) . . ?
O3 C24 C25 115.77(13) . . ?
C23 C24 C25 117.64(13) . . ?
F5 C25 F6 107.20(11) . . ?
F5 C25 F4 107.03(12) . . ?
F6 C25 F4 107.02(12) . . ?
F5 C25 C24 111.79(12) . . ?
F6 C25 C24 114.02(12) . . ?
F4 C25 C24 109.44(11) . . ?
C1 O2 C13 117.06(11) . . ?
C14 O4 C26 117.58(11) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 991428'
