# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_global
_database_code_depnum_ccdc_archive 'CCDC 1858383'
_audit_update_record             
;
2018-07-26 deposited with the CCDC.
2018-09-29 downloaded from the CCDC.
;
_audit_creation_method           'APEX2 v2014.1-1'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 F O2'
_chemical_formula_weight         192.18

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   4.9693(3)
_cell_length_b                   5.8579(3)
_cell_length_c                   31.3863(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     913.64(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7005
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29989
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.596
_diffrn_reflns_theta_max         28.759
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2375
_reflns_number_gt                1864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker Instrument Service v2014.5.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.2050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 605 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.5(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2375
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1060
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2684(6) 0.4479(4) 0.14537(9) 0.0481(6) Uani 1 1 d . . . . .
C2 C 0.0966(6) 0.4193(4) 0.17800(9) 0.0500(7) Uani 1 1 d . . . . .
H2 H 0.0901 0.5245 0.2002 0.060 Uiso 1 1 calc R U . . .
C3 C -0.0734(5) 0.2270(4) 0.17793(8) 0.0452(6) Uani 1 1 d . . . . .
C4 C -0.0682(5) 0.0753(4) 0.14466(7) 0.0412(6) Uani 1 1 d . . . . .
H4 H -0.1823 -0.0506 0.1448 0.049 Uiso 1 1 calc R U . . .
C5 C 0.1106(5) 0.1100(4) 0.11015(8) 0.0363(5) Uani 1 1 d . . . . .
C6 C 0.1219(5) -0.0435(4) 0.07521(7) 0.0401(5) Uani 1 1 d . . . . .
H6 H 0.0075 -0.1692 0.0744 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3000(5) -0.0074(4) 0.04273(7) 0.0401(6) Uani 1 1 d . . . . .
C8 C 0.4777(5) 0.1784(5) 0.04318(8) 0.0490(7) Uani 1 1 d . . . . .
H8 H 0.6000 0.1984 0.0211 0.059 Uiso 1 1 calc R U . . .
C9 C 0.4706(5) 0.3297(5) 0.07619(9) 0.0499(7) Uani 1 1 d . . . . .
H9 H 0.5879 0.4534 0.0764 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2871(5) 0.3005(4) 0.11003(8) 0.0408(5) Uani 1 1 d . . . . .
C11 C -0.4045(7) 0.0136(5) 0.21546(9) 0.0596(8) Uani 1 1 d . . . . .
H11A H -0.5239 0.0124 0.1914 0.089 Uiso 1 1 calc R U . . .
H11B H -0.5078 0.0195 0.2413 0.089 Uiso 1 1 calc R U . . .
H11C H -0.2968 -0.1224 0.2153 0.089 Uiso 1 1 calc R U . . .
F1 F 0.4397(4) 0.6295(3) 0.14581(6) 0.0725(6) Uani 1 1 d . . . . .
O1 O -0.2340(4) 0.2084(4) 0.21311(6) 0.0582(5) Uani 1 1 d . . . . .
O2 O 0.3180(4) -0.1498(3) 0.00781(6) 0.0533(5) Uani 1 1 d . . . . .
H2A H 0.1735 -0.2146 0.0042 0.080 Uiso 1 1 calc R U . . .


_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 1.344(4) . ?
C1 F1 1.362(3) . ?
C1 C10 1.409(4) . ?
C2 C3 1.408(4) . ?
C2 H2 0.9300 . ?
C3 O1 1.367(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.416(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.419(3) . ?
C5 C6 1.419(3) . ?
C6 C7 1.367(3) . ?
C6 H6 0.9300 . ?
C7 O2 1.380(3) . ?
C7 C8 1.401(3) . ?
C8 C9 1.364(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.410(4) . ?
C9 H9 0.9300 . ?
C11 O1 1.423(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
O2 H2A 0.8200 . ?

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 F1 119.1(2) . . ?
C2 C1 C10 124.4(2) . . ?
F1 C1 C10 116.4(2) . . ?
C1 C2 C3 118.7(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
O1 C3 C4 125.0(2) . . ?
O1 C3 C2 114.4(2) . . ?
C4 C3 C2 120.6(2) . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C10 120.2(2) . . ?
C4 C5 C6 121.6(2) . . ?
C10 C5 C6 118.2(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 O2 122.7(2) . . ?
C6 C7 C8 121.4(2) . . ?
O2 C7 C8 115.9(2) . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C1 C10 C9 124.1(2) . . ?
C1 C10 C5 116.0(2) . . ?
C9 C10 C5 119.8(2) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C3 O1 C11 116.97(19) . . ?
C7 O2 H2A 109.5 . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4



