# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_190902LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1957347'
loop_
_audit_author_name
_audit_author_address
'Meng-Yang Chang'
;Kaohsiung Medical University
Taiwan
;
_audit_update_record             
;
2019-10-03 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F O4'
_chemical_formula_weight         300.27

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      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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'

_cell_length_a                   4.0051(3)
_cell_length_b                   10.1298(8)
_cell_length_c                   16.3327(12)
_cell_angle_alpha                90
_cell_angle_beta                 92.222(3)
_cell_angle_gamma                90
_cell_volume                     662.13(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3887
_cell_measurement_theta_min      2.3664
_cell_measurement_theta_max      26.3172

_exptl_crystal_description       lamelar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6849
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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 8.3333
_diffrn_reflns_number            3830
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         26.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_point_group_measured_fraction_full 0.756
_reflns_number_total             1987
_reflns_number_gt                1898
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_max     0.483
_reflns_Friedel_fraction_full    0.517

_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       'APEX2 (Bruker AXS, 2010)'
_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-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  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)+(0.0439P)²+0.1217P] 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 594 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         1987
_refine_ls_number_parameters     201
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_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
F1 F 1.0360(4) 0.10593(16) 0.37284(10) 0.0273(4) Uani 1 1 d . . . . .
O1 O -0.3741(5) 0.43480(17) 0.95125(12) 0.0212(4) Uani 1 1 d . . . . .
O2 O 0.3373(4) 0.25726(17) 0.63708(10) 0.0175(4) Uani 1 1 d . . . . .
O3 O 0.5559(5) -0.13446(17) 0.61561(13) 0.0259(5) Uani 1 1 d . . . . .
O4 O -0.2552(5) 0.56258(18) 0.81865(12) 0.0229(4) Uani 1 1 d . . . . .
C1 C -0.4390(8) 0.3682(3) 1.02626(17) 0.0240(6) Uani 1 1 d . . . . .
H1 H -0.6073 0.2994 1.0159 0.036 Uiso 1 1 calc R U . . .
H6 H -0.5218 0.4318 1.0659 0.036 Uiso 1 1 calc R U . . .
H7 H -0.2322 0.3279 1.0484 0.036 Uiso 1 1 calc R U . . .
C2 C -0.2298(6) 0.3636(2) 0.89137(16) 0.0162(5) Uani 1 1 d . . . . .
C3 C -0.1602(6) 0.4329(3) 0.81935(16) 0.0178(6) Uani 1 1 d . . . . .
C4 C -0.0062(7) 0.3702(2) 0.75627(16) 0.0181(6) Uani 1 1 d . . . . .
H10 H 0.0434 0.4182 0.7082 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0786(7) 0.2354(2) 0.76235(16) 0.0160(6) Uani 1 1 d . . . . .
C6 C 0.2495(6) 0.1702(3) 0.69602(15) 0.0164(6) Uani 1 1 d . . . . .
C7 C 0.5121(6) 0.2138(2) 0.57160(15) 0.0150(6) Uani 1 1 d . . . . .
C8 C 0.5979(6) 0.0821(3) 0.56232(16) 0.0158(6) Uani 1 1 d . . . . .
C9 C 0.7771(6) 0.0456(3) 0.49428(16) 0.0180(6) Uani 1 1 d . . . . .
H13 H 0.8402 -0.0437 0.4863 0.022 Uiso 1 1 calc R U . . .
C10 C 0.8604(6) 0.1409(3) 0.43927(16) 0.0191(6) Uani 1 1 d . . . . .
C11 C 0.3209(7) 0.0394(3) 0.69034(16) 0.0177(6) Uani 1 1 d . . . . .
H2 H 0.2526 -0.0180 0.7325 0.021 Uiso 1 1 calc R U . . .
C12 C 0.4953(6) -0.0154(2) 0.62319(16) 0.0176(6) Uani 1 1 d . . . . .
C13 C -0.1814(9) 0.6385(3) 0.7476(2) 0.0314(7) Uani 1 1 d . . . . .
H3 H 0.0604 0.6388 0.7405 0.047 Uiso 1 1 calc R U . . .
H5 H -0.2596 0.7294 0.7545 0.047 Uiso 1 1 calc R U . . .
H4 H -0.2945 0.5994 0.6991 0.047 Uiso 1 1 calc R U . . .
C14 C -0.1498(7) 0.2306(3) 0.89721(16) 0.0191(6) Uani 1 1 d . . . . .
H8 H -0.1982 0.1826 0.9453 0.023 Uiso 1 1 calc R U . . .
C15 C 0.0011(7) 0.1674(2) 0.83273(16) 0.0192(6) Uani 1 1 d . . . . .
H9 H 0.0520 0.0760 0.8370 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5967(7) 0.3088(3) 0.51475(16) 0.0192(6) Uani 1 1 d . . . . .
H12 H 0.5331 0.3982 0.5221 0.023 Uiso 1 1 calc R U . . .
C17 C 0.7733(6) 0.2728(3) 0.44755(17) 0.0199(6) Uani 1 1 d . . . . .
H11 H 0.8337 0.3364 0.4080 0.024 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 1.362(3) . ?
O1 C2 1.362(3) . ?
O1 C1 1.431(3) . ?
O2 C6 1.362(3) . ?
O2 C7 1.373(3) . ?
O3 C12 1.237(3) . ?
O4 C3 1.367(3) . ?
O4 C13 1.433(4) . ?
C1 H1 0.9800 . ?
C1 H6 0.9800 . ?
C1 H7 0.9800 . ?
C2 C14 1.388(4) . ?
C2 C3 1.407(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.410(3) . ?
C4 H10 0.9500 . ?
C5 C15 1.385(4) . ?
C5 C6 1.462(4) . ?
C6 C11 1.359(3) . ?
C7 C8 1.388(3) . ?
C7 C16 1.388(4) . ?
C8 C9 1.396(4) . ?
C8 C12 1.471(4) . ?
C9 C10 1.369(4) . ?
C9 H13 0.9500 . ?
C10 C17 1.388(4) . ?
C11 C12 1.435(4) . ?
C11 H2 0.9500 . ?
C13 H3 0.9800 . ?
C13 H5 0.9800 . ?
C13 H4 0.9800 . ?
C14 C15 1.390(4) . ?
C14 H8 0.9500 . ?
C15 H9 0.9500 . ?
C16 C17 1.378(4) . ?
C16 H12 0.9500 . ?
C17 H11 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 O1 C1 117.5(2) . . ?
C6 O2 C7 119.73(19) . . ?
C3 O4 C13 117.2(2) . . ?
O1 C1 H1 109.5 . . ?
O1 C1 H6 109.5 . . ?
H1 C1 H6 109.5 . . ?
O1 C1 H7 109.5 . . ?
H1 C1 H7 109.5 . . ?
H6 C1 H7 109.5 . . ?
O1 C2 C14 124.6(2) . . ?
O1 C2 C3 116.1(2) . . ?
C14 C2 C3 119.3(3) . . ?
O4 C3 C4 124.7(2) . . ?
O4 C3 C2 115.0(2) . . ?
C4 C3 C2 120.3(2) . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H10 119.7 . . ?
C5 C4 H10 119.7 . . ?
C15 C5 C4 118.6(3) . . ?
C15 C5 C6 121.1(2) . . ?
C4 C5 C6 120.3(2) . . ?
C11 C6 O2 121.5(2) . . ?
C11 C6 C5 126.6(2) . . ?
O2 C6 C5 111.9(2) . . ?
O2 C7 C8 122.0(2) . . ?
O2 C7 C16 116.3(2) . . ?
C8 C7 C16 121.7(2) . . ?
C7 C8 C9 118.6(2) . . ?
C7 C8 C12 119.6(2) . . ?
C9 C8 C12 121.8(2) . . ?
C10 C9 C8 118.8(2) . . ?
C10 C9 H13 120.6 . . ?
C8 C9 H13 120.6 . . ?
F1 C10 C9 119.0(2) . . ?
F1 C10 C17 117.9(2) . . ?
C9 C10 C17 123.1(3) . . ?
C6 C11 C12 122.6(2) . . ?
C6 C11 H2 118.7 . . ?
C12 C11 H2 118.7 . . ?
O3 C12 C11 123.8(2) . . ?
O3 C12 C8 121.7(2) . . ?
C11 C12 C8 114.5(2) . . ?
O4 C13 H3 109.5 . . ?
O4 C13 H5 109.5 . . ?
H3 C13 H5 109.5 . . ?
O4 C13 H4 109.5 . . ?
H3 C13 H4 109.5 . . ?
H5 C13 H4 109.5 . . ?
C2 C14 C15 120.0(3) . . ?
C2 C14 H8 120.0 . . ?
C15 C14 H8 120.0 . . ?
C5 C15 C14 121.2(2) . . ?
C5 C15 H9 119.4 . . ?
C14 C15 H9 119.4 . . ?
C17 C16 C7 119.7(2) . . ?
C17 C16 H12 120.1 . . ?
C7 C16 H12 120.1 . . ?
C16 C17 C10 118.1(3) . . ?
C16 C17 H11 121.0 . . ?
C10 C17 H11 121.0 . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

