# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 2177594'
loop_
_audit_author_name
_audit_author_address
'Zhong-Wei Hou'
;Taizhou University
China
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2022-12-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H20 F N O5'
_chemical_formula_weight         337.34

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'
N N 0.0061 0.0033 '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           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   15.456(6)
_cell_length_b                   8.301(3)
_cell_length_c                   13.506(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.264(7)
_cell_angle_gamma                90.00
_cell_volume                     1693.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1706
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      21.90

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9734
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            8058
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2963
_reflns_number_gt                1928
_reflns_threshold_expression     >2sigma(I)

_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-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)+(0.0500P)²+0.3000P] 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         2963
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.29040(13) 0.6777(2) 0.43452(14) 0.0615(5) Uani 1 1 d . . .
F1 F 0.22996(9) 0.32941(16) 0.35361(10) 0.0764(4) Uani 1 1 d . . .
O1 O 0.14960(12) 0.6752(2) 0.33672(14) 0.0830(6) Uani 1 1 d . . .
O2 O 0.32286(11) 0.1259(2) 0.48014(15) 0.0878(6) Uani 1 1 d . . .
O3 O 0.21763(10) 0.10723(18) 0.57050(11) 0.0611(4) Uani 1 1 d . . .
O4 O 0.11178(12) 0.1264(2) 0.26169(13) 0.0835(6) Uani 1 1 d . . .
O5 O 0.06336(10) 0.07438(19) 0.40305(11) 0.0670(5) Uani 1 1 d . . .
C1 C 0.44600(19) 0.5432(5) 0.6690(3) 0.0987(11) Uani 1 1 d . . .
H1A H 0.5044 0.5491 0.7047 0.118 Uiso 1 1 calc R . .
C2 C 0.3872(2) 0.4547(4) 0.7100(2) 0.0900(9) Uani 1 1 d . . .
H2A H 0.4065 0.4011 0.7711 0.108 Uiso 1 1 calc R . .
C3 C 0.29924(17) 0.4453(3) 0.66053(17) 0.0637(6) Uani 1 1 d . . .
H3A H 0.2584 0.3887 0.6886 0.076 Uiso 1 1 calc R . .
C4 C 0.27382(14) 0.5219(2) 0.56853(15) 0.0485(5) Uani 1 1 d . . .
C5 C 0.33467(14) 0.6101(3) 0.52716(17) 0.0549(6) Uani 1 1 d . . .
C6 C 0.42298(16) 0.6244(4) 0.5771(2) 0.0780(8) Uani 1 1 d . . .
C7 C 0.49245(18) 0.7229(5) 0.5411(3) 0.1248(15) Uani 1 1 d . . .
H7A H 0.4669 0.7716 0.4771 0.187 Uiso 1 1 calc R . .
H7B H 0.5406 0.6543 0.5335 0.187 Uiso 1 1 calc R . .
H7C H 0.5140 0.8055 0.5899 0.187 Uiso 1 1 calc R . .
C8 C 0.3282(2) 0.7699(3) 0.3618(2) 0.0957(10) Uani 1 1 d . . .
H8A H 0.2820 0.8003 0.3055 0.144 Uiso 1 1 calc R . .
H8B H 0.3710 0.7050 0.3381 0.144 Uiso 1 1 calc R . .
H8C H 0.3564 0.8649 0.3941 0.144 Uiso 1 1 calc R . .
C9 C 0.20322(16) 0.6365(3) 0.41279(18) 0.0577(6) Uani 1 1 d . . .
C10 C 0.12282(15) 0.6436(3) 0.5536(2) 0.0692(7) Uani 1 1 d . . .
H10A H 0.1530 0.7417 0.5777 0.104 Uiso 1 1 calc R . .
H10B H 0.1088 0.5855 0.6096 0.104 Uiso 1 1 calc R . .
H10C H 0.0692 0.6685 0.5056 0.104 Uiso 1 1 calc R . .
C11 C 0.18304(13) 0.5394(2) 0.50201(15) 0.0482(5) Uani 1 1 d . . .
C12 C 0.13272(13) 0.3838(2) 0.46465(17) 0.0511(5) Uani 1 1 d . . .
H12A H 0.1133 0.3353 0.5215 0.061 Uiso 1 1 calc R . .
H12B H 0.0800 0.4130 0.4149 0.061 Uiso 1 1 calc R . .
C13 C 0.18260(14) 0.2558(3) 0.41756(16) 0.0524(5) Uani 1 1 d . . .
C14 C 0.25077(14) 0.1570(3) 0.49342(18) 0.0557(6) Uani 1 1 d . . .
C15 C 0.27651(18) 0.0137(3) 0.64727(19) 0.0826(8) Uani 1 1 d . . .
H15A H 0.2461 -0.0165 0.6994 0.124 Uiso 1 1 calc R . .
H15B H 0.3275 0.0773 0.6762 0.124 Uiso 1 1 calc R . .
H15C H 0.2949 -0.0814 0.6170 0.124 Uiso 1 1 calc R . .
C16 C 0.11623(14) 0.1425(3) 0.35007(17) 0.0537(6) Uani 1 1 d . . .
C17 C -0.00505(15) -0.0318(3) 0.34786(18) 0.0712(7) Uani 1 1 d . . .
H17A H -0.0391 -0.0748 0.3935 0.107 Uiso 1 1 calc R . .
H17B H 0.0220 -0.1186 0.3185 0.107 Uiso 1 1 calc R . .
H17C H -0.0433 0.0278 0.2952 0.107 Uiso 1 1 calc R . .


_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
N1 C9 1.360(3) . ?
N1 C5 1.409(3) . ?
N1 C8 1.461(3) . ?
F1 C13 1.387(2) . ?
O1 C9 1.218(3) . ?
O2 C14 1.194(3) . ?
O3 C14 1.320(3) . ?
O3 C15 1.451(3) . ?
O4 C16 1.188(3) . ?
O5 C16 1.322(2) . ?
O5 C17 1.455(2) . ?
C1 C2 1.373(4) . ?
C1 C6 1.391(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.399(3) . ?
C4 C11 1.504(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.510(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C11 1.536(3) . ?
C10 C11 1.541(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.537(3) . ?
C12 C13 1.528(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C16 1.540(3) . ?
C13 C14 1.541(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C9 N1 C5 111.32(18) . . ?
C9 N1 C8 120.4(2) . . ?
C5 N1 C8 128.1(2) . . ?
C14 O3 C15 116.20(19) . . ?
C16 O5 C17 116.58(17) . . ?
C2 C1 C6 123.6(3) . . ?
C2 C1 H1A 118.2 . . ?
C6 C1 H1A 118.2 . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 118.2(3) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 C11 129.4(2) . . ?
C5 C4 C11 109.39(18) . . ?
C6 C5 C4 121.6(2) . . ?
C6 C5 N1 129.6(2) . . ?
C4 C5 N1 108.80(19) . . ?
C1 C6 C5 115.4(3) . . ?
C1 C6 C7 119.0(3) . . ?
C5 C6 C7 125.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 125.5(2) . . ?
O1 C9 C11 125.8(2) . . ?
N1 C9 C11 108.64(19) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 C9 101.55(17) . . ?
C4 C11 C12 117.24(17) . . ?
C9 C11 C12 110.90(17) . . ?
C4 C11 C10 111.14(17) . . ?
C9 C11 C10 107.62(18) . . ?
C12 C11 C10 107.95(17) . . ?
C13 C12 C11 117.14(16) . . ?
C13 C12 H12A 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.3 . . ?
F1 C13 C12 109.43(17) . . ?
F1 C13 C16 105.89(17) . . ?
C12 C13 C16 109.84(17) . . ?
F1 C13 C14 105.77(17) . . ?
C12 C13 C14 115.31(18) . . ?
C16 C13 C14 110.13(17) . . ?
O2 C14 O3 125.5(2) . . ?
O2 C14 C13 122.9(2) . . ?
O3 C14 C13 111.46(18) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 125.8(2) . . ?
O4 C16 C13 123.5(2) . . ?
O5 C16 C13 110.58(18) . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035
