# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_4fin
_database_code_depnum_ccdc_archive 'CCDC 2194506'
loop_
_audit_author_name
_audit_author_address
'F. Sanz'
;Universidad de salamanca
Spain
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 F N2 O5'
_chemical_formula_sum            'C15 H17 F N2 O5'
_chemical_formula_weight         324.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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)
_symmetry_space_group_name_Hall  P2yb

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

_cell_length_a                   10.4371(6)
_cell_length_b                   9.9381(4)
_cell_length_c                   15.5195(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.104(4)
_cell_angle_gamma                90.00
_cell_volume                     1561.23(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1379
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      53.84

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.833
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7012
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         67.55
_reflns_number_total             3463
_reflns_number_gt                2776
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_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)+(0.0447P)²+0.0771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(2)
_refine_ls_number_reflns         3463
_refine_ls_number_parameters     459
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1010
_refine_ls_wR_factor_gt          0.0915
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
F1 F -0.4912(3) -0.0257(4) -0.0444(2) 0.1164(10) Uani 1 1 d . . .
O1 O 0.1035(2) 0.1495(3) 0.06653(15) 0.0653(6) Uani 1 1 d . . .
O2 O 0.3827(3) -0.1456(3) 0.1864(2) 0.0799(8) Uani 1 1 d . . .
O3 O 0.2520(3) -0.1120(3) 0.28019(16) 0.0674(7) Uani 1 1 d . . .
O4 O -0.0387(4) 0.3620(4) 0.2483(3) 0.1398(17) Uani 1 1 d . . .
O5 O 0.1619(4) 0.3262(3) 0.3136(3) 0.1091(12) Uani 1 1 d . . .
N1 N 0.2285(3) 0.1660(3) 0.1356(2) 0.0643(7) Uani 1 1 d . . .
N2 N 0.0608(4) 0.2964(3) 0.2594(2) 0.0745(9) Uani 1 1 d . . .
C2 C 0.0042(3) 0.2040(3) 0.1047(2) 0.0551(8) Uani 1 1 d . . .
C3 C 0.0556(3) 0.1708(3) 0.2056(2) 0.0510(7) Uani 1 1 d . . .
C3A C 0.1877(3) 0.1068(3) 0.2124(2) 0.0533(7) Uani 1 1 d . . .
C4 C 0.1864(3) -0.0461(3) 0.2011(2) 0.0502(7) Uani 1 1 d . . .
C5 C 0.2739(4) -0.0723(4) 0.1349(2) 0.0616(9) Uani 1 1 d . . .
C6 C 0.3169(4) 0.0657(4) 0.1112(3) 0.0725(10) Uani 1 1 d . . .
H6A H 0.4075 0.0828 0.1433 0.087 Uiso 1 1 calc R . .
H6B H 0.3118 0.0706 0.0481 0.087 Uiso 1 1 calc R . .
C8 C 0.3401(4) -0.2086(4) 0.2571(3) 0.0759(11) Uani 1 1 d . . .
C9 C 0.2688(6) -0.3373(4) 0.2281(4) 0.1070(17) Uani 1 1 d . . .
H9A H 0.1913 -0.3192 0.1816 0.161 Uiso 1 1 calc R . .
H9B H 0.2434 -0.3779 0.2776 0.161 Uiso 1 1 calc R . .
H9C H 0.3258 -0.3974 0.2064 0.161 Uiso 1 1 calc R . .
C10 C 0.4566(5) -0.2243(6) 0.3358(3) 0.1096(18) Uani 1 1 d . . .
H10A H 0.5222 -0.2800 0.3196 0.164 Uiso 1 1 calc R . .
H10B H 0.4281 -0.2654 0.3839 0.164 Uiso 1 1 calc R . .
H10C H 0.4937 -0.1374 0.3540 0.164 Uiso 1 1 calc R . .
C11 C -0.1273(3) 0.1442(3) 0.0616(2) 0.0557(8) Uani 1 1 d . . .
C12 C -0.2433(4) 0.2120(4) 0.0626(2) 0.0645(9) Uani 1 1 d . . .
H12 H -0.2385 0.2971 0.0881 0.077 Uiso 1 1 calc R . .
C13 C -0.3654(4) 0.1559(5) 0.0267(3) 0.0768(11) Uani 1 1 d . . .
H13 H -0.4425 0.2020 0.0279 0.092 Uiso 1 1 calc R . .
C14 C -0.3703(4) 0.0330(5) -0.0102(3) 0.0779(11) Uani 1 1 d . . .
C15 C -0.2600(4) -0.0383(5) -0.0152(3) 0.0838(11) Uani 1 1 d . . .
H15 H -0.2668 -0.1221 -0.0426 0.101 Uiso 1 1 calc R . .
C16 C -0.1385(4) 0.0185(4) 0.0217(3) 0.0726(10) Uani 1 1 d . . .
H16 H -0.0623 -0.0287 0.0198 0.087 Uiso 1 1 calc R . .
F1' F 0.2681(3) 0.1452(4) 0.88441(19) 0.1357(13) Uani 1 1 d . . .
O1' O -0.0499(2) 0.5515(2) 0.60425(14) 0.0538(5) Uani 1 1 d . . .
O2' O -0.3895(2) 0.4709(3) 0.39431(19) 0.0740(7) Uani 1 1 d . . .
O3' O -0.2351(2) 0.3192(2) 0.38272(18) 0.0724(7) Uani 1 1 d . . .
O4' O 0.2807(3) 0.4455(3) 0.5019(2) 0.0812(8) Uani 1 1 d . . .
O5' O 0.1515(3) 0.5904(2) 0.42146(18) 0.0735(7) Uani 1 1 d . . .
N1' N -0.0996(3) 0.6065(2) 0.51266(19) 0.0548(6) Uani 1 1 d . . .
N2' N 0.1726(3) 0.4963(3) 0.47328(19) 0.0563(7) Uani 1 1 d . . .
C2' C 0.0799(3) 0.5057(3) 0.6048(2) 0.0493(7) Uani 1 1 d . . .
C3' C 0.0623(3) 0.4426(3) 0.5108(2) 0.0487(7) Uani 1 1 d . . .
C3A' C -0.0745(3) 0.4870(3) 0.4613(2) 0.0507(7) Uani 1 1 d . . .
C4' C -0.1847(3) 0.3859(3) 0.4647(2) 0.0527(7) Uani 1 1 d . . .
C5' C -0.2994(4) 0.4718(3) 0.4796(3) 0.0593(8) Uani 1 1 d . . .
C6' C -0.2439(4) 0.6129(3) 0.4994(3) 0.0663(9) Uani 1 1 d . . .
H6'1 H -0.2817 0.6726 0.4503 0.080 Uiso 1 1 calc R . .
H6'2 H -0.2658 0.6476 0.5525 0.080 Uiso 1 1 calc R . .
C8' C -0.3734(4) 0.3475(3) 0.3533(3) 0.0650(9) Uani 1 1 d . . .
C9' C -0.4525(5) 0.2363(5) 0.3824(4) 0.0987(15) Uani 1 1 d . . .
H9'1 H -0.4138 0.2141 0.4434 0.148 Uiso 1 1 calc R . .
H9'2 H -0.4521 0.1583 0.3460 0.148 Uiso 1 1 calc R . .
H9'3 H -0.5418 0.2660 0.3763 0.148 Uiso 1 1 calc R . .
C10' C -0.4084(6) 0.3667(6) 0.2549(3) 0.1100(17) Uani 1 1 d . . .
H10D H -0.5019 0.3810 0.2344 0.165 Uiso 1 1 calc R . .
H10E H -0.3837 0.2880 0.2269 0.165 Uiso 1 1 calc R . .
H10F H -0.3622 0.4435 0.2401 0.165 Uiso 1 1 calc R . .
C11' C 0.1279(3) 0.4120(3) 0.6814(2) 0.0509(7) Uani 1 1 d . . .
C12' C 0.2510(4) 0.4280(6) 0.7372(3) 0.0908(15) Uani 1 1 d . . .
H12' H 0.3026 0.5010 0.7292 0.109 Uiso 1 1 calc R . .
C13' C 0.3000(4) 0.3379(8) 0.8050(3) 0.113(2) Uani 1 1 d . . .
H13' H 0.3846 0.3481 0.8414 0.136 Uiso 1 1 calc R . .
C14' C 0.2226(4) 0.2351(5) 0.8172(3) 0.0849(13) Uani 1 1 d . . .
C15' C 0.0992(5) 0.2149(4) 0.7656(3) 0.0778(11) Uani 1 1 d . . .
H15' H 0.0476 0.1433 0.7758 0.093 Uiso 1 1 calc R . .
C16' C 0.0525(4) 0.3057(4) 0.6964(2) 0.0651(9) Uani 1 1 d . . .
H16' H -0.0316 0.2938 0.6598 0.078 Uiso 1 1 calc R . .
H2 H -0.005(3) 0.299(4) 0.099(2) 0.062(9) Uiso 1 1 d . . .
H3A H 0.260(3) 0.128(4) 0.274(2) 0.060(9) Uiso 1 1 d . . .
H3 H 0.001(3) 0.116(3) 0.225(2) 0.042(8) Uiso 1 1 d . . .
H4 H 0.101(3) -0.084(3) 0.179(2) 0.046(8) Uiso 1 1 d . . .
H5 H 0.229(3) -0.138(4) 0.083(3) 0.075(11) Uiso 1 1 d . . .
H2' H 0.144(3) 0.581(4) 0.614(2) 0.066(10) Uiso 1 1 d . . .
H3A' H -0.083(3) 0.520(3) 0.400(2) 0.049(8) Uiso 1 1 d . . .
H3' H 0.075(3) 0.345(3) 0.5141(19) 0.034(7) Uiso 1 1 d . . .
H4' H -0.156(3) 0.315(4) 0.514(2) 0.061(9) Uiso 1 1 d . . .
H5' H -0.341(3) 0.422(4) 0.522(2) 0.061(10) Uiso 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
F1 C14 1.374(5) . ?
O1 C2 1.421(4) . ?
O1 N1 1.482(4) . ?
O2 C5 1.419(5) . ?
O2 C8 1.425(5) . ?
O3 C4 1.412(4) . ?
O3 C8 1.434(4) . ?
O4 N2 1.202(5) . ?
O5 N2 1.215(5) . ?
N1 C6 1.469(5) . ?
N1 C3A 1.481(4) . ?
N2 C3 1.495(5) . ?
C2 C11 1.496(5) . ?
C2 C3 1.562(5) . ?
C2 H2 0.95(4) . ?
C3 C3A 1.499(5) . ?
C3 H3 0.90(3) . ?
C3A C4 1.530(5) . ?
C3A H3A 1.09(4) . ?
C4 C5 1.555(4) . ?
C4 H4 0.95(3) . ?
C5 C6 1.516(6) . ?
C5 H5 1.05(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C8 C9 1.493(7) . ?
C8 C10 1.507(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C16 1.386(6) . ?
C11 C12 1.389(5) . ?
C12 C13 1.378(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.345(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(6) . ?
C15 C16 1.379(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
F1' C14' 1.368(5) . ?
O1' C2' 1.427(4) . ?
O1' N1' 1.493(4) . ?
O2' C8' 1.410(4) . ?
O2' C5' 1.424(5) . ?
O3' C4' 1.418(4) . ?
O3' C8' 1.432(4) . ?
O4' N2' 1.217(4) . ?
O5' N2' 1.218(4) . ?
N1' C6' 1.471(5) . ?
N1' C3A' 1.489(4) . ?
N2' C3' 1.508(4) . ?
C2' C11' 1.497(5) . ?
C2' C3' 1.557(4) . ?
C2' H2' 0.99(4) . ?
C3' C3A' 1.513(4) . ?
C3' H3' 0.98(3) . ?
C3A' C4' 1.538(5) . ?
C3A' H3A' 0.99(3) . ?
C4' C5' 1.533(5) . ?
C4' H4' 1.03(4) . ?
C5' C6' 1.520(5) . ?
C5' H5' 1.01(4) . ?
C6' H6'1 0.9700 . ?
C6' H6'2 0.9700 . ?
C8' C10' 1.494(6) . ?
C8' C9' 1.513(6) . ?
C9' H9'1 0.9600 . ?
C9' H9'2 0.9600 . ?
C9' H9'3 0.9600 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' C16' 1.371(5) . ?
C11' C12' 1.373(5) . ?
C12' C13' 1.382(7) . ?
C12' H12' 0.9300 . ?
C13' C14' 1.344(8) . ?
C13' H13' 0.9300 . ?
C14' C15' 1.355(6) . ?
C15' C16' 1.395(5) . ?
C15' H15' 0.9300 . ?
C16' H16' 0.9300 . ?

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 N1 105.0(2) . . ?
C5 O2 C8 107.6(2) . . ?
C4 O3 C8 107.3(3) . . ?
C6 N1 C3A 105.0(3) . . ?
C6 N1 O1 103.6(3) . . ?
C3A N1 O1 99.4(2) . . ?
O4 N2 O5 122.8(4) . . ?
O4 N2 C3 117.4(4) . . ?
O5 N2 C3 119.8(3) . . ?
O1 C2 C11 110.2(3) . . ?
O1 C2 C3 103.3(3) . . ?
C11 C2 C3 114.7(3) . . ?
O1 C2 H2 114(2) . . ?
C11 C2 H2 107(2) . . ?
C3 C2 H2 107(2) . . ?
N2 C3 C3A 114.1(3) . . ?
N2 C3 C2 109.9(3) . . ?
C3A C3 C2 104.2(3) . . ?
N2 C3 H3 105(2) . . ?
C3A C3 H3 111.8(19) . . ?
C2 C3 H3 112(2) . . ?
N1 C3A C3 102.4(3) . . ?
N1 C3A C4 107.4(3) . . ?
C3 C3A C4 115.5(3) . . ?
N1 C3A H3A 111.2(18) . . ?
C3 C3A H3A 113.9(18) . . ?
C4 C3A H3A 106(2) . . ?
O3 C4 C3A 111.9(3) . . ?
O3 C4 C5 105.0(3) . . ?
C3A C4 C5 104.6(3) . . ?
O3 C4 H4 110.3(19) . . ?
C3A C4 H4 114.7(19) . . ?
C5 C4 H4 109.8(18) . . ?
O2 C5 C6 111.0(3) . . ?
O2 C5 C4 103.4(3) . . ?
C6 C5 C4 105.4(3) . . ?
O2 C5 H5 105(2) . . ?
C6 C5 H5 119(2) . . ?
C4 C5 H5 112.2(19) . . ?
N1 C6 C5 108.1(3) . . ?
N1 C6 H6A 110.1 . . ?
C5 C6 H6A 110.1 . . ?
N1 C6 H6B 110.1 . . ?
C5 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
O2 C8 O3 103.8(3) . . ?
O2 C8 C9 111.7(3) . . ?
O3 C8 C9 110.2(4) . . ?
O2 C8 C10 109.2(4) . . ?
O3 C8 C10 107.9(4) . . ?
C9 C8 C10 113.6(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 117.6(3) . . ?
C16 C11 C2 121.8(3) . . ?
C12 C11 C2 120.6(3) . . ?
C13 C12 C11 121.5(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 118.4(4) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C15 123.3(4) . . ?
C13 C14 F1 119.1(4) . . ?
C15 C14 F1 117.7(4) . . ?
C14 C15 C16 117.7(4) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 H15 121.1 . . ?
C15 C16 C11 121.6(4) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C2' O1' N1' 103.4(2) . . ?
C8' O2' C5' 107.5(3) . . ?
C4' O3' C8' 108.6(3) . . ?
C6' N1' C3A' 105.5(3) . . ?
C6' N1' O1' 104.8(3) . . ?
C3A' N1' O1' 98.8(2) . . ?
O4' N2' O5' 124.2(3) . . ?
O4' N2' C3' 116.0(3) . . ?
O5' N2' C3' 119.7(3) . . ?
O1' C2' C11' 109.7(2) . . ?
O1' C2' C3' 103.2(2) . . ?
C11' C2' C3' 115.7(2) . . ?
O1' C2' H2' 112(2) . . ?
C11' C2' H2' 106(2) . . ?
C3' C2' H2' 111(2) . . ?
N2' C3' C3A' 114.5(3) . . ?
N2' C3' C2' 107.0(2) . . ?
C3A' C3' C2' 103.8(2) . . ?
N2' C3' H3' 105.5(15) . . ?
C3A' C3' H3' 114.4(16) . . ?
C2' C3' H3' 111.5(17) . . ?
N1' C3A' C3' 103.2(2) . . ?
N1' C3A' C4' 105.8(3) . . ?
C3' C3A' C4' 114.4(2) . . ?
N1' C3A' H3A' 104.9(19) . . ?
C3' C3A' H3A' 116.2(18) . . ?
C4' C3A' H3A' 111.0(18) . . ?
O3' C4' C5' 105.2(3) . . ?
O3' C4' C3A' 113.0(3) . . ?
C5' C4' C3A' 105.0(3) . . ?
O3' C4' H4' 109(2) . . ?
C5' C4' H4' 111.3(19) . . ?
C3A' C4' H4' 113(2) . . ?
O2' C5' C6' 109.1(3) . . ?
O2' C5' C4' 102.7(3) . . ?
C6' C5' C4' 105.8(3) . . ?
O2' C5' H5' 108(2) . . ?
C6' C5' H5' 121(2) . . ?
C4' C5' H5' 108(2) . . ?
N1' C6' C5' 108.3(2) . . ?
N1' C6' H6'1 110.0 . . ?
C5' C6' H6'1 110.0 . . ?
N1' C6' H6'2 110.0 . . ?
C5' C6' H6'2 110.0 . . ?
H6'1 C6' H6'2 108.4 . . ?
O2' C8' O3' 104.4(3) . . ?
O2' C8' C10' 108.9(3) . . ?
O3' C8' C10' 109.1(4) . . ?
O2' C8' C9' 111.5(3) . . ?
O3' C8' C9' 110.0(3) . . ?
C10' C8' C9' 112.5(4) . . ?
C8' C9' H9'1 109.5 . . ?
C8' C9' H9'2 109.5 . . ?
H9'1 C9' H9'2 109.5 . . ?
C8' C9' H9'3 109.5 . . ?
H9'1 C9' H9'3 109.5 . . ?
H9'2 C9' H9'3 109.5 . . ?
C8' C10' H10D 109.5 . . ?
C8' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C8' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C16' C11' C12' 118.0(4) . . ?
C16' C11' C2' 121.3(3) . . ?
C12' C11' C2' 120.6(3) . . ?
C11' C12' C13' 121.5(5) . . ?
C11' C12' H12' 119.3 . . ?
C13' C12' H12' 119.3 . . ?
C14' C13' C12' 118.4(4) . . ?
C14' C13' H13' 120.8 . . ?
C12' C13' H13' 120.8 . . ?
C13' C14' C15' 123.1(4) . . ?
C13' C14' F1' 119.6(4) . . ?
C15' C14' F1' 117.3(5) . . ?
C14' C15' C16' 117.6(4) . . ?
C14' C15' H15' 121.2 . . ?
C16' C15' H15' 121.2 . . ?
C11' C16' C15' 121.4(3) . . ?
C11' C16' H16' 119.3 . . ?
C15' C16' H16' 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.886
_diffrn_reflns_theta_full        67.55
_diffrn_measured_fraction_theta_full 0.886
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_4fin_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2194507'
loop_
_audit_author_name
_audit_author_address
'F. Sanz'
;Universidad de salamanca
Spain
;
_audit_update_record             
;
2022-08-03 deposited with the CCDC.	2024-07-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 F N2 O5'
_chemical_formula_sum            'C15 H17 F N2 O5'
_chemical_formula_weight         324.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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)
_symmetry_space_group_name_Hall  P2yb

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

_cell_length_a                   6.3774(3)
_cell_length_b                   8.9628(5)
_cell_length_c                   13.9221(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.748(4)
_cell_angle_gamma                90.00
_cell_volume                     784.29(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2275
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      59.33

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.909
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6847
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         65.79
_reflns_number_total             2238
_reflns_number_gt                2047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Mercury 4.0.0 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_chemical_absolute_configuration rm

_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)+(0.0278P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0141(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         2238
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0728
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.0624(2) 0.21445(15) 0.48494(10) 0.0479(4) Uani 1 1 d . . .
O2 O 0.2311(3) 0.27639(19) 0.79316(10) 0.0665(5) Uani 1 1 d . . .
O3 O 0.4991(3) 0.4132(2) 0.75102(11) 0.0768(5) Uani 1 1 d . . .
O4 O 0.4556(3) 0.5201(2) 0.37402(13) 0.0792(6) Uani 1 1 d . . .
O5 O 0.5581(2) 0.3098(3) 0.44183(13) 0.0786(5) Uani 1 1 d . . .
N1 N 0.1486(2) 0.23619(19) 0.58638(11) 0.0448(4) Uani 1 1 d . . .
N2 N 0.4433(3) 0.4198(2) 0.43258(13) 0.0532(5) Uani 1 1 d . . .
C2 C 0.0643(3) 0.3554(2) 0.43609(14) 0.0412(4) Uani 1 1 d . . .
C3 C 0.2669(3) 0.4328(2) 0.49065(14) 0.0406(4) Uani 1 1 d . . .
C3A C 0.3188(3) 0.3495(2) 0.58779(14) 0.0429(5) Uani 1 1 d . . .
C4 C 0.3178(4) 0.4418(3) 0.67968(16) 0.0564(6) Uani 1 1 d . . .
C5 C 0.1301(4) 0.3804(3) 0.72292(17) 0.0605(6) Uani 1 1 d . . .
C8 C 0.4370(4) 0.3319(3) 0.83033(16) 0.0693(7) Uani 1 1 d . . .
C9 C 0.5867(6) 0.2025(5) 0.8541(2) 0.1059(11) Uani 1 1 d . . .
H9A H 0.5774 0.1385 0.7982 0.159 Uiso 1 1 calc R . .
H9B H 0.5485 0.1474 0.9077 0.159 Uiso 1 1 calc R . .
H9C H 0.7296 0.2390 0.8715 0.159 Uiso 1 1 calc R . .
C10 C 0.4336(6) 0.4366(5) 0.9147(2) 0.1105(12) Uani 1 1 d . . .
H10A H 0.5749 0.4726 0.9377 0.166 Uiso 1 1 calc R . .
H10B H 0.3823 0.3845 0.9663 0.166 Uiso 1 1 calc R . .
H10C H 0.3415 0.5193 0.8937 0.166 Uiso 1 1 calc R . .
C6 C -0.0092(3) 0.3022(3) 0.64046(15) 0.0572(6) Uani 1 1 d . . .
H6A H -0.0951 0.2258 0.6643 0.069 Uiso 1 1 calc R . .
H6B H -0.1017 0.3720 0.6002 0.069 Uiso 1 1 calc R . .
C11 C 0.0477(3) 0.3311(2) 0.32895(14) 0.0445(5) Uani 1 1 d . . .
C12 C -0.0798(3) 0.4250(3) 0.26521(15) 0.0597(6) Uani 1 1 d . . .
H12 H -0.1612 0.4974 0.2896 0.072 Uiso 1 1 calc R . .
C13 C -0.0876(4) 0.4125(4) 0.16585(18) 0.0783(8) Uani 1 1 d . . .
H13 H -0.1717 0.4766 0.1230 0.094 Uiso 1 1 calc R . .
C14 C 0.0307(4) 0.3041(4) 0.13215(17) 0.0768(8) Uani 1 1 d . . .
C15 C 0.1560(4) 0.2082(3) 0.19184(19) 0.0725(7) Uani 1 1 d . . .
H15 H 0.2348 0.1353 0.1664 0.087 Uiso 1 1 calc R . .
C16 C 0.1638(3) 0.2217(3) 0.29138(16) 0.0571(6) Uani 1 1 d . . .
H16 H 0.2478 0.1566 0.3334 0.069 Uiso 1 1 calc R . .
F1 F 0.0251(3) 0.2918(3) 0.03406(10) 0.1229(8) Uani 1 1 d . . .
H2 H -0.051(3) 0.417(3) 0.4490(14) 0.049(5) Uiso 1 1 d . . .
H3 H 0.250(4) 0.541(3) 0.4982(16) 0.060(6) Uiso 1 1 d . . .
H3A H 0.450(4) 0.302(3) 0.5876(14) 0.048(5) Uiso 1 1 d . . .
H4 H 0.311(4) 0.551(3) 0.6638(18) 0.070(7) Uiso 1 1 d . . .
H5 H 0.055(4) 0.464(3) 0.7528(18) 0.078(8) Uiso 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
O1 C2 1.435(2) . ?
O1 N1 1.439(2) . ?
O2 C8 1.418(3) . ?
O2 C5 1.424(3) . ?
O3 C4 1.414(3) . ?
O3 C8 1.434(3) . ?
O4 N2 1.225(2) . ?
O5 N2 1.222(3) . ?
N1 C6 1.478(3) . ?
N1 C3A 1.485(2) . ?
N2 C3 1.497(3) . ?
C2 C11 1.493(3) . ?
C2 C3 1.548(3) . ?
C2 H2 0.96(2) . ?
C3 C3A 1.531(3) . ?
C3 H3 0.98(3) . ?
C3A C4 1.524(3) . ?
C3A H3A 0.94(2) . ?
C4 C5 1.530(3) . ?
C4 H4 1.00(3) . ?
C5 C6 1.501(3) . ?
C5 H5 1.01(3) . ?
C8 C9 1.503(5) . ?
C8 C10 1.506(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C11 C12 1.383(3) . ?
C11 C16 1.383(3) . ?
C12 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.361(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.358(4) . ?
C14 F1 1.365(3) . ?
C15 C16 1.384(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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 N1 108.26(13) . . ?
C8 O2 C5 107.71(18) . . ?
C4 O3 C8 109.45(17) . . ?
O1 N1 C6 111.98(14) . . ?
O1 N1 C3A 105.22(14) . . ?
C6 N1 C3A 106.17(17) . . ?
O5 N2 O4 123.89(19) . . ?
O5 N2 C3 119.84(19) . . ?
O4 N2 C3 116.2(2) . . ?
O1 C2 C11 109.90(16) . . ?
O1 C2 C3 103.60(14) . . ?
C11 C2 C3 117.86(16) . . ?
O1 C2 H2 110.4(13) . . ?
C11 C2 H2 110.1(12) . . ?
C3 C2 H2 104.6(12) . . ?
N2 C3 C3A 111.66(16) . . ?
N2 C3 C2 109.96(16) . . ?
C3A C3 C2 104.63(16) . . ?
N2 C3 H3 104.0(15) . . ?
C3A C3 H3 113.4(13) . . ?
C2 C3 H3 113.4(14) . . ?
N1 C3A C4 105.97(16) . . ?
N1 C3A C3 105.87(15) . . ?
C4 C3A C3 116.48(18) . . ?
N1 C3A H3A 109.6(14) . . ?
C4 C3A H3A 112.4(12) . . ?
C3 C3A H3A 106.3(12) . . ?
O3 C4 C3A 111.8(2) . . ?
O3 C4 C5 105.06(18) . . ?
C3A C4 C5 104.47(18) . . ?
O3 C4 H4 109.4(14) . . ?
C3A C4 H4 110.5(15) . . ?
C5 C4 H4 115.4(15) . . ?
O2 C5 C6 111.1(2) . . ?
O2 C5 C4 102.28(19) . . ?
C6 C5 C4 105.55(18) . . ?
O2 C5 H5 113.0(14) . . ?
C6 C5 H5 113.6(15) . . ?
C4 C5 H5 110.4(16) . . ?
O2 C8 O3 104.89(16) . . ?
O2 C8 C9 108.9(2) . . ?
O3 C8 C9 108.3(3) . . ?
O2 C8 C10 111.6(2) . . ?
O3 C8 C10 109.0(2) . . ?
C9 C8 C10 113.7(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C6 C5 102.16(17) . . ?
N1 C6 H6A 111.3 . . ?
C5 C6 H6A 111.3 . . ?
N1 C6 H6B 111.3 . . ?
C5 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C12 C11 C16 118.87(19) . . ?
C12 C11 C2 119.12(18) . . ?
C16 C11 C2 121.94(18) . . ?
C13 C12 C11 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 118.4(2) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C15 C14 C13 123.0(2) . . ?
C15 C14 F1 118.3(3) . . ?
C13 C14 F1 118.7(3) . . ?
C14 C15 C16 118.4(2) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C11 C16 C15 120.7(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        65.79
_diffrn_measured_fraction_theta_full 0.932
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.031
