# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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. 
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data_a61102ba
_database_code_depnum_ccdc_archive 'CCDC 1526176'
_audit_update_record             
;
2017-01-09 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 F2 O4'
_chemical_formula_weight         372.35

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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.326(4)
_cell_length_b                   11.032(4)
_cell_length_c                   13.445(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1828.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3083
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.939
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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            4989
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.388
_diffrn_reflns_theta_max         25.094
_diffrn_reflns_theta_full        25.094
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measured_fraction_theta_full 0.954
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_Laue_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.687
_diffrn_reflns_point_group_measured_fraction_full 0.687
_reflns_number_total             2237
_reflns_number_gt                2134
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.377
_reflns_Friedel_fraction_max     0.395
_reflns_Friedel_fraction_full    0.395

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0587P)²+0.2150P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 561 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.6(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2237
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0937
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.075
_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_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
F1 F 0.17893(15) -0.09042(16) 0.58139(17) 0.0759(7) Uani 1 1 d . . . . .
F2 F 0.19291(17) -0.16541(16) 0.7295(2) 0.0826(8) Uani 1 1 d . . . . .
O1 O -0.05420(17) 0.00119(19) 0.7962(2) 0.0675(7) Uani 1 1 d . . . . .
O2 O -0.04236(16) -0.10420(19) 0.5960(2) 0.0639(6) Uani 1 1 d . . . . .
O3 O 0.0048(2) -0.2586(2) 0.6948(3) 0.0871(9) Uani 1 1 d . . . . .
O4 O 0.59247(16) 0.15592(18) 0.51580(18) 0.0561(5) Uani 1 1 d . . . . .
C1 C 0.0231(2) 0.0645(3) 0.7759(2) 0.0461(6) Uani 1 1 d . . . . .
C2 C 0.1198(2) 0.0290(2) 0.7160(2) 0.0432(6) Uani 1 1 d . . . . .
C3 C 0.19116(19) 0.1230(2) 0.71183(19) 0.0377(6) Uani 1 1 d . . . . .
C4 C 0.14345(19) 0.2267(2) 0.76936(19) 0.0379(5) Uani 1 1 d . . . . .
C5 C 0.1857(2) 0.3382(2) 0.7917(2) 0.0413(6) Uani 1 1 d . . . . .
H5 H 0.2547 0.3596 0.7698 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1238(2) 0.4197(2) 0.8479(2) 0.0456(6) Uani 1 1 d . . . . .
C7 C 0.0229(2) 0.3842(3) 0.8822(2) 0.0495(7) Uani 1 1 d . . . . .
H7 H -0.0181 0.4386 0.9193 0.059 Uiso 1 1 calc R U . . .
C8 C -0.0188(2) 0.2704(3) 0.8631(2) 0.0481(7) Uani 1 1 d . . . . .
H8 H -0.0861 0.2471 0.8878 0.058 Uiso 1 1 calc R U . . .
C9 C 0.04261(19) 0.1925(2) 0.8062(2) 0.0420(6) Uani 1 1 d . . . . .
C10 C 0.1290(2) -0.0936(2) 0.6716(3) 0.0525(7) Uani 1 1 d . . . . .
C11 C 0.0220(2) -0.1629(2) 0.6571(3) 0.0568(8) Uani 1 1 d . . . . .
C12 C -0.1472(3) -0.1615(3) 0.5792(4) 0.0845(13) Uani 1 1 d . . . . .
H12A H -0.1374 -0.2361 0.5422 0.101 Uiso 1 1 calc R U . . .
H12B H -0.1805 -0.1812 0.6425 0.101 Uiso 1 1 calc R U . . .
C13 C -0.2164(4) -0.0804(4) 0.5244(6) 0.124(2) Uani 1 1 d . . . . .
H13A H -0.1780 -0.0499 0.4675 0.186 Uiso 1 1 calc R U . . .
H13B H -0.2374 -0.0140 0.5663 0.186 Uiso 1 1 calc R U . . .
H13C H -0.2800 -0.1232 0.5027 0.186 Uiso 1 1 calc R U . . .
C14 C 0.29732(18) 0.1328(2) 0.6632(2) 0.0374(5) Uani 1 1 d . . . . .
C15 C 0.32354(19) 0.2378(2) 0.6111(2) 0.0402(6) Uani 1 1 d . . . . .
H15 H 0.2740 0.3014 0.6094 0.048 Uiso 1 1 calc R U . . .
C16 C 0.4210(2) 0.2499(2) 0.5619(2) 0.0431(6) Uani 1 1 d . . . . .
H16 H 0.4366 0.3205 0.5268 0.052 Uiso 1 1 calc R U . . .
C17 C 0.49607(19) 0.1556(2) 0.5650(2) 0.0407(6) Uani 1 1 d . . . . .
C18 C 0.47305(19) 0.0535(2) 0.6198(2) 0.0426(6) Uani 1 1 d . . . . .
H18 H 0.5246 -0.0077 0.6248 0.051 Uiso 1 1 calc R U . . .
C19 C 0.3753(2) 0.0406(2) 0.6671(2) 0.0416(6) Uani 1 1 d . . . . .
H19 H 0.3605 -0.0302 0.7022 0.050 Uiso 1 1 calc R U . . .
C20 C 0.6115(3) 0.2505(3) 0.4458(3) 0.0707(9) Uani 1 1 d . . . . .
H20A H 0.6124 0.3271 0.4796 0.106 Uiso 1 1 calc R U . . .
H20B H 0.5549 0.2505 0.3968 0.106 Uiso 1 1 calc R U . . .
H20C H 0.6802 0.2377 0.4138 0.106 Uiso 1 1 calc R U . . .
C21 C 0.1685(3) 0.5442(3) 0.8682(3) 0.0651(9) Uani 1 1 d . . . . .
H21A H 0.1755 0.5559 0.9386 0.098 Uiso 1 1 calc R U . . .
H21B H 0.1202 0.6041 0.8414 0.098 Uiso 1 1 calc R U . . .
H21C H 0.2385 0.5521 0.8374 0.098 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
F1 C10 1.361(4) . ?
F2 C10 1.362(4) . ?
O1 C1 1.213(3) . ?
O2 C11 1.313(4) . ?
O2 C12 1.456(4) . ?
O3 C11 1.191(4) . ?
O4 C17 1.360(3) . ?
O4 C20 1.425(4) . ?
C1 C9 1.488(4) . ?
C1 C2 1.491(4) . ?
C2 C3 1.361(3) . ?
C2 C10 1.483(4) . ?
C3 C14 1.467(3) . ?
C3 C4 1.501(3) . ?
C4 C5 1.369(4) . ?
C4 C9 1.390(4) . ?
C5 C6 1.401(4) . ?
C6 C7 1.383(4) . ?
C6 C21 1.505(4) . ?
C7 C8 1.381(4) . ?
C8 C9 1.377(4) . ?
C10 C11 1.537(4) . ?
C12 C13 1.440(7) . ?
C14 C15 1.392(4) . ?
C14 C19 1.400(3) . ?
C15 C16 1.378(4) . ?
C16 C17 1.393(3) . ?
C17 C18 1.376(4) . ?
C18 C19 1.370(4) . ?

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
C11 O2 C12 114.8(3) . . ?
C17 O4 C20 117.9(2) . . ?
O1 C1 C9 127.7(3) . . ?
O1 C1 C2 126.8(3) . . ?
C9 C1 C2 105.5(2) . . ?
C3 C2 C10 128.9(2) . . ?
C3 C2 C1 109.8(2) . . ?
C10 C2 C1 121.2(2) . . ?
C2 C3 C14 130.6(2) . . ?
C2 C3 C4 107.8(2) . . ?
C14 C3 C4 121.5(2) . . ?
C5 C4 C9 120.4(2) . . ?
C5 C4 C3 130.4(2) . . ?
C9 C4 C3 109.1(2) . . ?
C4 C5 C6 119.2(2) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 C21 121.8(3) . . ?
C5 C6 C21 118.9(2) . . ?
C8 C7 C6 122.0(2) . . ?
C9 C8 C7 117.8(3) . . ?
C8 C9 C4 121.3(2) . . ?
C8 C9 C1 130.9(2) . . ?
C4 C9 C1 107.7(2) . . ?
F1 C10 F2 105.3(2) . . ?
F1 C10 C2 111.7(2) . . ?
F2 C10 C2 110.2(3) . . ?
F1 C10 C11 106.7(3) . . ?
F2 C10 C11 106.2(2) . . ?
C2 C10 C11 116.1(2) . . ?
O3 C11 O2 126.6(3) . . ?
O3 C11 C10 122.7(3) . . ?
O2 C11 C10 110.7(3) . . ?
C13 C12 O2 109.6(3) . . ?
C15 C14 C19 117.7(2) . . ?
C15 C14 C3 119.5(2) . . ?
C19 C14 C3 122.8(2) . . ?
C16 C15 C14 121.6(2) . . ?
C15 C16 C17 119.5(2) . . ?
O4 C17 C18 116.3(2) . . ?
O4 C17 C16 124.3(2) . . ?
C18 C17 C16 119.4(2) . . ?
C19 C18 C17 121.0(2) . . ?
C18 C19 C14 120.7(2) . . ?

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
O1 C1 C2 C3 -178.1(3) . . . . ?
C9 C1 C2 C3 1.2(3) . . . . ?
O1 C1 C2 C10 1.4(5) . . . . ?
C9 C1 C2 C10 -179.3(3) . . . . ?
C10 C2 C3 C14 0.1(5) . . . . ?
C1 C2 C3 C14 179.5(3) . . . . ?
C10 C2 C3 C4 -179.8(3) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C2 C3 C4 C5 176.0(3) . . . . ?
C14 C3 C4 C5 -3.8(4) . . . . ?
C2 C3 C4 C9 -0.7(3) . . . . ?
C14 C3 C4 C9 179.4(2) . . . . ?
C9 C4 C5 C6 -3.2(4) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C4 C5 C6 C7 2.0(4) . . . . ?
C4 C5 C6 C21 -177.1(3) . . . . ?
C5 C6 C7 C8 0.3(4) . . . . ?
C21 C6 C7 C8 179.4(3) . . . . ?
C6 C7 C8 C9 -1.4(5) . . . . ?
C7 C8 C9 C4 0.2(4) . . . . ?
C7 C8 C9 C1 177.4(3) . . . . ?
C5 C4 C9 C8 2.1(4) . . . . ?
C3 C4 C9 C8 179.2(3) . . . . ?
C5 C4 C9 C1 -175.7(3) . . . . ?
C3 C4 C9 C1 1.5(3) . . . . ?
O1 C1 C9 C8 0.2(6) . . . . ?
C2 C1 C9 C8 -179.1(3) . . . . ?
O1 C1 C9 C4 177.7(3) . . . . ?
C2 C1 C9 C4 -1.6(3) . . . . ?
C3 C2 C10 F1 -36.4(4) . . . . ?
C1 C2 C10 F1 144.2(3) . . . . ?
C3 C2 C10 F2 80.2(4) . . . . ?
C1 C2 C10 F2 -99.1(3) . . . . ?
C3 C2 C10 C11 -159.0(3) . . . . ?
C1 C2 C10 C11 21.6(4) . . . . ?
C12 O2 C11 O3 3.9(5) . . . . ?
C12 O2 C11 C10 -178.6(3) . . . . ?
F1 C10 C11 O3 114.0(4) . . . . ?
F2 C10 C11 O3 2.1(5) . . . . ?
C2 C10 C11 O3 -120.7(4) . . . . ?
F1 C10 C11 O2 -63.6(3) . . . . ?
F2 C10 C11 O2 -175.5(3) . . . . ?
C2 C10 C11 O2 61.7(4) . . . . ?
C11 O2 C12 C13 171.0(4) . . . . ?
C2 C3 C14 C15 137.2(3) . . . . ?
C4 C3 C14 C15 -43.0(3) . . . . ?
C2 C3 C14 C19 -43.3(4) . . . . ?
C4 C3 C14 C19 136.5(3) . . . . ?
C19 C14 C15 C16 2.3(4) . . . . ?
C3 C14 C15 C16 -178.2(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C20 O4 C17 C18 170.0(3) . . . . ?
C20 O4 C17 C16 -9.2(4) . . . . ?
C15 C16 C17 O4 177.1(3) . . . . ?
C15 C16 C17 C18 -2.1(4) . . . . ?
O4 C17 C18 C19 -175.9(2) . . . . ?
C16 C17 C18 C19 3.4(4) . . . . ?
C17 C18 C19 C14 -1.8(4) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?
C3 C14 C19 C18 179.5(2) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033



