# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_cu_d8v19901_0m
_database_code_depnum_ccdc_archive 'CCDC 2094077'
loop_
_audit_author_name
_audit_author_address
'Jie Sun'
;Shanghai institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai
China
;
_audit_update_record             
;
2021-07-02 deposited with the CCDC.	2021-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 F N2 O5'
_chemical_formula_weight         372.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
F F 0.0727 0.0534 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'

_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'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   9.5302(3)
_cell_length_b                   9.5302(3)
_cell_length_c                   19.3236(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1755.06(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9974
_cell_measurement_theta_min      9.380
_cell_measurement_theta_max      140.093

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.931
_shelx_estimated_absorpt_T_min   0.836
_shelx_estimated_absorpt_T_max   0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5199
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            16115
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.640
_diffrn_reflns_theta_max         67.489
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             3121
_reflns_number_gt                2995
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.930
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.978

_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-2013 (Sheldrick, 2013)'
_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)+(0.0335P)²+0.1536P] 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
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1385 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.03(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3121
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0713
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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 0.08258(18) -0.17728(17) 0.39218(8) 0.0746(5) Uani 1 1 d . . . . .
O1 O 0.5814(2) -0.0652(2) 0.46747(11) 0.0737(5) Uani 1 1 d . . . . .
O2 O 0.32921(15) 0.25721(16) 0.52986(8) 0.0498(4) Uani 1 1 d . . . . .
O3 O 0.4340(2) 0.5806(2) 0.48881(9) 0.0672(5) Uani 1 1 d . . . . .
O4 O 0.7318(2) 0.2264(3) 0.45947(12) 0.0934(7) Uani 1 1 d . . . . .
O5 O 0.7998(2) 0.1412(4) 0.55509(16) 0.1172(10) Uani 1 1 d . . . . .
N1 N 0.3499(2) 0.5860(2) 0.59820(10) 0.0546(5) Uani 1 1 d . . . . .
H1 H 0.3520 0.5473 0.6384 0.065 Uiso 1 1 calc R U . . .
N2 N 0.7089(2) 0.1732(3) 0.51505(12) 0.0700(6) Uani 1 1 d . . . . .
C1 C 0.2734(2) 0.1478(2) 0.49302(10) 0.0445(5) Uani 1 1 d . . . . .
C2 C 0.1297(2) 0.1480(2) 0.48351(12) 0.0502(5) Uani 1 1 d . . . . .
H2 H 0.0758 0.2215 0.5006 0.060 Uiso 1 1 calc R U . . .
C3 C 0.0670(3) 0.0399(3) 0.44892(13) 0.0551(6) Uani 1 1 d . . . . .
H3 H -0.0296 0.0397 0.4421 0.066 Uiso 1 1 calc R U . . .
C4 C 0.1480(3) -0.0689(3) 0.42421(12) 0.0542(6) Uani 1 1 d . . . . .
C5 C 0.2894(3) -0.0733(3) 0.43330(12) 0.0555(6) Uani 1 1 d . . . . .
H5 H 0.3417 -0.1482 0.4164 0.067 Uiso 1 1 calc R U . . .
C6 C 0.3548(2) 0.0369(2) 0.46867(11) 0.0487(5) Uani 1 1 d . . . . .
C7 C 0.5051(2) 0.0292(3) 0.48534(12) 0.0546(6) Uani 1 1 d . . . . .
C8 C 0.5568(2) 0.1455(3) 0.53404(12) 0.0539(6) Uani 1 1 d . . . . .
C9 C 0.4761(2) 0.2827(2) 0.51971(12) 0.0493(5) Uani 1 1 d . . . . .
H9 H 0.4921 0.3113 0.4716 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5130(3) 0.4031(3) 0.56728(13) 0.0565(6) Uani 1 1 d . . . . .
H10A H 0.4929 0.3772 0.6148 0.068 Uiso 1 1 calc R U . . .
H10B H 0.6124 0.4235 0.5637 0.068 Uiso 1 1 calc R U . . .
C11 C 0.4292(2) 0.5319(3) 0.54805(12) 0.0513(5) Uani 1 1 d . . . . .
C12 C 0.5458(3) 0.0941(3) 0.60832(14) 0.0701(7) Uani 1 1 d . . . . .
H12A H 0.5921 0.0051 0.6125 0.105 Uiso 1 1 calc R U . . .
H12B H 0.4487 0.0841 0.6207 0.105 Uiso 1 1 calc R U . . .
H12C H 0.5896 0.1608 0.6387 0.105 Uiso 1 1 calc R U . . .
C13 C 0.2604(3) 0.7072(3) 0.58818(14) 0.0616(7) Uani 1 1 d . . . . .
H13A H 0.3041 0.7684 0.5544 0.074 Uiso 1 1 calc R U . . .
H13B H 0.2551 0.7584 0.6315 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1133(3) 0.6755(2) 0.56445(11) 0.0543(6) Uani 1 1 d . . . . .
C15 C 0.0716(3) 0.5455(3) 0.54059(14) 0.0615(6) Uani 1 1 d . . . . .
H15 H 0.1362 0.4724 0.5392 0.074 Uiso 1 1 calc R U . . .
C16 C -0.0646(3) 0.5222(3) 0.51874(16) 0.0723(7) Uani 1 1 d . . . . .
H16 H -0.0908 0.4336 0.5033 0.087 Uiso 1 1 calc R U . . .
C17 C -0.1609(3) 0.6285(4) 0.51974(17) 0.0795(8) Uani 1 1 d . . . . .
H17 H -0.2524 0.6129 0.5049 0.095 Uiso 1 1 calc R U . . .
C18 C -0.1206(4) 0.7588(4) 0.5429(2) 0.0857(10) Uani 1 1 d . . . . .
H18 H -0.1854 0.8317 0.5437 0.103 Uiso 1 1 calc R U . . .
C19 C 0.0145(4) 0.7824(3) 0.56489(15) 0.0717(8) Uani 1 1 d . . . . .
H19 H 0.0400 0.8713 0.5803 0.086 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 C4 1.356(3) . ?
O1 C7 1.207(3) . ?
O2 C1 1.370(3) . ?
O2 C9 1.434(3) . ?
O3 C11 1.236(3) . ?
O4 N2 1.208(3) . ?
O5 N2 1.200(3) . ?
N1 C11 1.333(3) . ?
N1 C13 1.449(3) . ?
N1 H1 0.8600 . ?
N2 C8 1.519(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(4) . ?
C5 C6 1.400(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.470(3) . ?
C7 C8 1.536(4) . ?
C8 C12 1.520(3) . ?
C8 C9 1.541(3) . ?
C9 C10 1.512(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.510(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.506(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.380(4) . ?
C14 C19 1.388(4) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.374(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(5) . ?
C18 H18 0.9300 . ?
C19 H19 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
C1 O2 C9 115.87(16) . . ?
C11 N1 C13 123.1(2) . . ?
C11 N1 H1 118.5 . . ?
C13 N1 H1 118.5 . . ?
O5 N2 O4 123.4(3) . . ?
O5 N2 C8 119.3(3) . . ?
O4 N2 C8 117.4(2) . . ?
O2 C1 C2 116.90(18) . . ?
O2 C1 C6 122.48(19) . . ?
C2 C1 C6 120.5(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
F1 C4 C5 119.4(2) . . ?
F1 C4 C3 118.3(2) . . ?
C5 C4 C3 122.3(2) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 C7 120.5(2) . . ?
C5 C6 C7 120.2(2) . . ?
O1 C7 C6 124.2(2) . . ?
O1 C7 C8 121.3(2) . . ?
C6 C7 C8 114.24(18) . . ?
N2 C8 C12 110.5(2) . . ?
N2 C8 C7 106.47(19) . . ?
C12 C8 C7 108.9(2) . . ?
N2 C8 C9 106.6(2) . . ?
C12 C8 C9 114.1(2) . . ?
C7 C8 C9 110.00(18) . . ?
O2 C9 C10 105.80(18) . . ?
O2 C9 C8 108.61(18) . . ?
C10 C9 C8 114.74(19) . . ?
O2 C9 H9 109.2 . . ?
C10 C9 H9 109.2 . . ?
C8 C9 H9 109.2 . . ?
C11 C10 C9 110.14(18) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O3 C11 N1 123.2(2) . . ?
O3 C11 C10 120.9(2) . . ?
N1 C11 C10 115.8(2) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 115.4(2) . . ?
N1 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N1 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C19 117.8(3) . . ?
C15 C14 C13 123.4(2) . . ?
C19 C14 C13 118.8(2) . . ?
C14 C15 C16 121.1(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C17 C16 C15 120.5(3) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 120.7(3) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C14 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?

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
C9 O2 C1 C2 -159.49(19) . . . . ?
C9 O2 C1 C6 23.5(3) . . . . ?
O2 C1 C2 C3 -178.2(2) . . . . ?
C6 C1 C2 C3 -1.1(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 F1 177.7(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
F1 C4 C5 C6 -177.7(2) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
O2 C1 C6 C5 178.0(2) . . . . ?
C2 C1 C6 C5 1.1(3) . . . . ?
O2 C1 C6 C7 3.6(3) . . . . ?
C2 C1 C6 C7 -173.3(2) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 174.1(2) . . . . ?
C1 C6 C7 O1 178.2(2) . . . . ?
C5 C6 C7 O1 3.8(3) . . . . ?
C1 C6 C7 C8 3.7(3) . . . . ?
C5 C6 C7 C8 -170.6(2) . . . . ?
O5 N2 C8 C12 6.7(4) . . . . ?
O4 N2 C8 C12 -173.6(3) . . . . ?
O5 N2 C8 C7 -111.4(3) . . . . ?
O4 N2 C8 C7 68.4(3) . . . . ?
O5 N2 C8 C9 131.2(3) . . . . ?
O4 N2 C8 C9 -49.1(3) . . . . ?
O1 C7 C8 N2 36.0(3) . . . . ?
C6 C7 C8 N2 -149.3(2) . . . . ?
O1 C7 C8 C12 -83.1(3) . . . . ?
C6 C7 C8 C12 91.5(2) . . . . ?
O1 C7 C8 C9 151.2(2) . . . . ?
C6 C7 C8 C9 -34.2(3) . . . . ?
C1 O2 C9 C10 -177.94(17) . . . . ?
C1 O2 C9 C8 -54.3(2) . . . . ?
N2 C8 C9 O2 173.91(18) . . . . ?
C12 C8 C9 O2 -63.9(3) . . . . ?
C7 C8 C9 O2 58.9(2) . . . . ?
N2 C8 C9 C10 -68.0(2) . . . . ?
C12 C8 C9 C10 54.3(3) . . . . ?
C7 C8 C9 C10 177.0(2) . . . . ?
O2 C9 C10 C11 -61.0(2) . . . . ?
C8 C9 C10 C11 179.34(19) . . . . ?
C13 N1 C11 O3 0.4(4) . . . . ?
C13 N1 C11 C10 -178.4(2) . . . . ?
C9 C10 C11 O3 -56.4(3) . . . . ?
C9 C10 C11 N1 122.5(2) . . . . ?
C11 N1 C13 C14 89.6(3) . . . . ?
N1 C13 C14 C15 -12.3(3) . . . . ?
N1 C13 C14 C19 169.2(2) . . . . ?
C19 C14 C15 C16 -0.9(4) . . . . ?
C13 C14 C15 C16 -179.4(2) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C15 C16 C17 C18 -0.2(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 -0.2(5) . . . . ?
C15 C14 C19 C18 0.6(4) . . . . ?
C13 C14 C19 C18 179.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C12 H12B F1 0.96 2.62 3.574(3) 172.4 3
C10 H10A O3 0.97 2.55 3.445(3) 152.6 3_655
N1 H1 O3 0.86 2.31 3.150(3) 164.8 3_655
N1 H1 O3 0.86 2.31 3.150(3) 164.8 3_655
C10 H10A O3 0.97 2.55 3.445(3) 152.6 3_655
C12 H12B F1 0.96 2.62 3.574(3) 172.4 3

_refine_diff_density_max         0.090
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.020

_shelxl_version_number           2013-4



