# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_BA52m
_database_code_depnum_ccdc_archive 'CCDC 1434563'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-03-04 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         'C18 H13 F O4'
_chemical_formula_sum            'C18 H13 F O4'
_chemical_formula_weight         312.28

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.1761(5)
_cell_length_b                   11.9692(7)
_cell_length_c                   15.1398(9)
_cell_angle_alpha                90
_cell_angle_beta                 96.3430(10)
_cell_angle_gamma                90
_cell_volume                     1472.53(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8279
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.21

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16820
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.174
_diffrn_reflns_theta_max         28.305
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3547
_reflns_number_gt                2998
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0865P)²+0.3503P] 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_number_reflns         3547
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1574
_refine_ls_wR_factor_gt          0.1496
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.23822(18) 0.46142(13) 0.63609(9) 0.0471(3) Uani 1 1 d . . . . .
C2 C 0.3153(2) 0.56483(13) 0.64157(10) 0.0526(4) Uani 1 1 d . . . . .
H2 H 0.3406 0.5985 0.6968 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3549(3) 0.61851(15) 0.56582(12) 0.0643(4) Uani 1 1 d . . . . .
H3 H 0.4094 0.6868 0.5692 0.077 Uiso 1 1 calc R U . . .
C4 C 0.3111(3) 0.56761(17) 0.48547(11) 0.0654(5) Uani 1 1 d . . . . .
C5 C 0.2330(3) 0.46629(18) 0.47674(11) 0.0677(5) Uani 1 1 d . . . . .
H5 H 0.2034 0.4351 0.4210 0.081 Uiso 1 1 calc R U . . .
C6 C 0.1996(2) 0.41173(15) 0.55313(11) 0.0582(4) Uani 1 1 d . . . . .
H6 H 0.1509 0.3414 0.5492 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2017(2) 0.39891(13) 0.71648(10) 0.0524(4) Uani 1 1 d . . . . .
C8 C 0.19699(17) 0.45969(12) 0.80343(9) 0.0442(3) Uani 1 1 d . . . . .
C9 C 0.27663(17) 0.41094(12) 0.87567(10) 0.0449(3) Uani 1 1 d . . . . .
H9 H 0.3297 0.3447 0.8639 0.054 Uiso 1 1 calc R U . . .
C10 C 0.29509(16) 0.44255(12) 0.96867(9) 0.0435(3) Uani 1 1 d . . . . .
C11 C 0.35882(19) 0.36290(14) 1.03152(11) 0.0540(4) Uani 1 1 d . . . . .
H11 H 0.3855 0.2919 1.0128 0.065 Uiso 1 1 calc R U . . .
C12 C 0.3821(2) 0.38897(18) 1.12037(12) 0.0627(5) Uani 1 1 d . . . . .
H12 H 0.4248 0.3355 1.1612 0.075 Uiso 1 1 calc R U . . .
C13 C 0.3429(2) 0.49353(17) 1.14960(10) 0.0602(5) Uani 1 1 d . . . . .
H13 H 0.3565 0.5095 1.2101 0.072 Uiso 1 1 calc R U . . .
C14 C 0.2835(2) 0.57478(14) 1.08960(9) 0.0529(4) Uani 1 1 d . . . . .
C15 C 0.26159(17) 0.54894(12) 0.99863(8) 0.0435(3) Uani 1 1 d . . . . .
C16 C 0.06985(19) 0.62241(14) 0.88554(10) 0.0506(4) Uani 1 1 d . . . . .
H16A H 0.0289 0.6961 0.8680 0.061 Uiso 1 1 calc R U . . .
H16B H -0.0103 0.5877 0.9196 0.061 Uiso 1 1 calc R U . . .
C17 C 0.08207(18) 0.55411(14) 0.80300(9) 0.0498(4) Uani 1 1 d . . . . .
C18 C 0.2465(4) 0.7093(2) 1.20167(13) 0.0965(8) Uani 1 1 d . . . . .
H18A H 0.1670 0.6645 1.2277 0.145 Uiso 1 1 calc R U . . .
H18B H 0.2195 0.7869 1.2070 0.145 Uiso 1 1 calc R U . . .
H18C H 0.3540 0.6955 1.2320 0.145 Uiso 1 1 calc R U . . .
F1 F 0.3484(2) 0.62050(12) 0.41092(8) 0.0991(5) Uani 1 1 d . . . . .
O1 O 0.21954(13) 0.63458(9) 0.94112(7) 0.0500(3) Uani 1 1 d . . . . .
O2 O -0.01454(18) 0.57241(16) 0.73832(8) 0.0866(5) Uani 1 1 d . . . . .
O3 O 0.1810(2) 0.29837(11) 0.71412(9) 0.0895(5) Uani 1 1 d . . . . .
O4 O 0.2449(2) 0.68127(11) 1.11047(8) 0.0781(4) 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 C2 1.387(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.487(2) . ?
C2 C3 1.384(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3 0.9300 . ?
C4 F1 1.358(2) . ?
C4 C5 1.370(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O3 1.215(2) . ?
C7 C8 1.5084(19) . ?
C8 C9 1.343(2) . ?
C8 C17 1.469(2) . ?
C9 C10 1.450(2) . ?
C9 H9 0.9300 . ?
C10 C15 1.389(2) . ?
C10 C11 1.406(2) . ?
C11 C12 1.373(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.377(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9300 . ?
C14 O4 1.359(2) . ?
C14 C15 1.4036(19) . ?
C15 O1 1.3642(17) . ?
C16 O1 1.4140(18) . ?
C16 C17 1.506(2) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.2083(18) . ?
C18 O4 1.420(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C2 C1 C6 119.39(15) . . ?
C2 C1 C7 122.07(13) . . ?
C6 C1 C7 118.48(15) . . ?
C3 C2 C1 120.73(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 117.81(17) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
F1 C4 C5 118.53(17) . . ?
F1 C4 C3 117.98(19) . . ?
C5 C4 C3 123.48(16) . . ?
C4 C5 C6 118.10(16) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 120.42(17) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O3 C7 C1 120.94(14) . . ?
O3 C7 C8 119.10(15) . . ?
C1 C7 C8 119.91(13) . . ?
C9 C8 C17 126.17(13) . . ?
C9 C8 C7 116.38(13) . . ?
C17 C8 C7 116.44(12) . . ?
C8 C9 C10 131.81(14) . . ?
C8 C9 H9 114.1 . . ?
C10 C9 H9 114.1 . . ?
C15 C10 C11 118.18(14) . . ?
C15 C10 C9 123.60(13) . . ?
C11 C10 C9 118.13(14) . . ?
C12 C11 C10 120.65(16) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 120.61(15) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C14 120.38(15) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
O4 C14 C13 125.53(15) . . ?
O4 C14 C15 115.29(14) . . ?
C13 C14 C15 119.17(16) . . ?
O1 C15 C10 121.68(12) . . ?
O1 C15 C14 117.16(14) . . ?
C10 C15 C14 120.94(13) . . ?
O1 C16 C17 114.66(12) . . ?
O1 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
O1 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
O2 C17 C8 120.23(14) . . ?
O2 C17 C16 118.48(14) . . ?
C8 C17 C16 120.99(12) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 O1 C16 116.29(11) . . ?
C14 O4 C18 118.07(17) . . ?

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
C6 C1 C2 C3 -0.4(2) . . . . ?
C7 C1 C2 C3 176.81(16) . . . . ?
C1 C2 C3 C4 1.9(3) . . . . ?
C2 C3 C4 F1 179.42(16) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
F1 C4 C5 C6 178.28(17) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 2.7(3) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C7 C1 C6 C5 -179.28(16) . . . . ?
C2 C1 C7 O3 -157.86(18) . . . . ?
C6 C1 C7 O3 19.4(3) . . . . ?
C2 C1 C7 C8 19.6(2) . . . . ?
C6 C1 C7 C8 -163.15(15) . . . . ?
O3 C7 C8 C9 43.4(2) . . . . ?
C1 C7 C8 C9 -134.13(15) . . . . ?
O3 C7 C8 C17 -125.83(19) . . . . ?
C1 C7 C8 C17 56.66(19) . . . . ?
C17 C8 C9 C10 -10.3(3) . . . . ?
C7 C8 C9 C10 -178.30(14) . . . . ?
C8 C9 C10 C15 -16.0(2) . . . . ?
C8 C9 C10 C11 167.52(15) . . . . ?
C15 C10 C11 C12 2.0(2) . . . . ?
C9 C10 C11 C12 178.66(14) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C11 C12 C13 C14 -1.7(3) . . . . ?
C12 C13 C14 O4 -178.18(16) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C11 C10 C15 O1 171.58(13) . . . . ?
C9 C10 C15 O1 -4.9(2) . . . . ?
C11 C10 C15 C14 -2.9(2) . . . . ?
C9 C10 C15 C14 -179.35(13) . . . . ?
O4 C14 C15 O1 5.9(2) . . . . ?
C13 C14 C15 O1 -173.21(13) . . . . ?
O4 C14 C15 C10 -179.36(14) . . . . ?
C13 C14 C15 C10 1.5(2) . . . . ?
C9 C8 C17 O2 -160.24(18) . . . . ?
C7 C8 C17 O2 7.8(2) . . . . ?
C9 C8 C17 C16 13.4(2) . . . . ?
C7 C8 C17 C16 -178.60(14) . . . . ?
O1 C16 C17 O2 -152.72(17) . . . . ?
O1 C16 C17 C8 33.5(2) . . . . ?
C10 C15 O1 C16 64.17(18) . . . . ?
C14 C15 O1 C16 -121.14(14) . . . . ?
C17 C16 O1 C15 -83.08(16) . . . . ?
C13 C14 O4 C18 -7.9(3) . . . . ?
C15 C14 O4 C18 173.03(18) . . . . ?

_refine_diff_density_max         0.291
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.047

