# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_pn140b
_database_code_depnum_ccdc_archive 'CCDC 2395307'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2025-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 F2 N O4'
_chemical_formula_weight         365.37

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   16.7661(2)
_cell_length_b                   6.89850(9)
_cell_length_c                   16.2957(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.2959(14)
_cell_angle_gamma                90
_cell_volume                     1841.55(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(2)
_cell_measurement_reflns_used    14875
_cell_measurement_theta_min      2.7050
_cell_measurement_theta_max      76.2620

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.892
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84452
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17724
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.697
_diffrn_reflns_theta_max         76.473
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3734
_reflns_number_gt                3578
_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       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0548P)²+0.5380P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00083(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3734
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_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
F23 F 0.69590(4) 0.53548(9) 0.58470(4) 0.02677(17) Uani 1 1 d . . . . .
F24 F 0.85905(4) 0.49985(10) 0.58302(4) 0.03274(18) Uani 1 1 d . . . . .
O14 O 0.56376(4) 0.48688(11) 0.38651(5) 0.02585(18) Uani 1 1 d . . . . .
O17 O 0.57103(5) 0.33726(11) 0.51027(5) 0.02889(19) Uani 1 1 d . . . . .
O19 O 0.89468(5) 0.67282(14) 0.39707(5) 0.0352(2) Uani 1 1 d . . . . .
O22 O 0.92680(5) 0.37894(14) 0.45553(6) 0.0395(2) Uani 1 1 d . . . . .
N6 N 0.74750(6) 0.88060(14) 0.50342(6) 0.0265(2) Uani 1 1 d . . . . .
C7 C 0.73258(6) 0.44304(16) 0.36993(6) 0.0218(2) Uani 1 1 d . . . . .
C13 C 0.59705(6) 0.44967(15) 0.46624(6) 0.0215(2) Uani 1 1 d . . . . .
C3 C 0.74779(6) 0.46624(15) 0.46494(6) 0.0209(2) Uani 1 1 d . . . . .
H3 H 0.754180 0.332543 0.489164 0.025 Uiso 1 1 calc R U . . .
C5 C 0.67308(6) 0.77793(15) 0.48354(6) 0.0227(2) Uani 1 1 d . . . . .
C2 C 0.82744(6) 0.57691(16) 0.50319(6) 0.0245(2) Uani 1 1 d . . . . .
C4 C 0.67691(6) 0.56132(15) 0.49680(6) 0.0209(2) Uani 1 1 d . . . . .
C12 C 0.72045(7) 0.59994(17) 0.31483(7) 0.0259(2) Uani 1 1 d . . . . .
H12 H 0.720435 0.728037 0.336235 0.031 Uiso 1 1 calc R U . . .
C1 C 0.81662(7) 0.79411(17) 0.51544(7) 0.0272(2) Uani 1 1 d . . . . .
C18 C 0.89062(7) 0.52983(17) 0.45010(7) 0.0288(2) Uani 1 1 d . . . . .
C8 C 0.73269(8) 0.25717(18) 0.33733(7) 0.0325(3) Uani 1 1 d . . . . .
H8 H 0.741262 0.148978 0.374226 0.039 Uiso 1 1 calc R U . . .
C15 C 0.49194(7) 0.37129(17) 0.34973(7) 0.0284(2) Uani 1 1 d . . . . .
H15A H 0.445394 0.406723 0.375255 0.034 Uiso 1 1 calc R U . . .
H15B H 0.503624 0.231561 0.359622 0.034 Uiso 1 1 calc R U . . .
C25 C 0.60407(7) 0.87815(17) 0.46409(8) 0.0306(3) Uani 1 1 d . . . . .
H25A H 0.605524 1.015815 0.463781 0.037 Uiso 1 1 calc R U . . .
H25B H 0.553211 0.812241 0.450481 0.037 Uiso 1 1 calc R U . . .
C11 C 0.70836(7) 0.5700(2) 0.22877(7) 0.0333(3) Uani 1 1 d . . . . .
H11 H 0.700113 0.677772 0.191612 0.040 Uiso 1 1 calc R U . . .
C16 C 0.47205(8) 0.41368(19) 0.25726(8) 0.0351(3) Uani 1 1 d . . . . .
H16A H 0.430221 0.322856 0.228855 0.053 Uiso 1 1 calc R U . . .
H16B H 0.521378 0.399214 0.234610 0.053 Uiso 1 1 calc R U . . .
H16C H 0.451549 0.546661 0.247959 0.053 Uiso 1 1 calc R U . . .
C10 C 0.70829(9) 0.3840(2) 0.19688(8) 0.0416(3) Uani 1 1 d . . . . .
H10 H 0.699987 0.363808 0.138004 0.050 Uiso 1 1 calc R U . . .
C9 C 0.72035(10) 0.2280(2) 0.25114(8) 0.0440(3) Uani 1 1 d . . . . .
H9 H 0.720210 0.100128 0.229495 0.053 Uiso 1 1 calc R U . . .
C26 C 0.89257(8) 0.9114(2) 0.54733(10) 0.0429(3) Uani 1 1 d . . . . .
H26A H 0.901075 1.001541 0.503523 0.064 Uiso 1 1 calc R U . . .
H26B H 0.939633 0.824307 0.562097 0.064 Uiso 1 1 calc R U . . .
H26C H 0.886459 0.984612 0.597156 0.064 Uiso 1 1 calc R U . . .
C20 C 0.94249(9) 0.6356(3) 0.33378(9) 0.0525(4) Uani 1 1 d . . . . .
H20A H 0.920731 0.521450 0.299369 0.063 Uiso 1 1 calc R U . . .
H20B H 1.000234 0.610265 0.360825 0.063 Uiso 1 1 calc R U . . .
C21 C 0.93577(12) 0.8140(3) 0.28010(11) 0.0697(6) Uani 1 1 d . . . . .
H21A H 0.970446 0.799643 0.239069 0.105 Uiso 1 1 calc R U . . .
H21B H 0.953559 0.927134 0.315639 0.105 Uiso 1 1 calc R U . . .
H21C H 0.878905 0.831631 0.250520 0.105 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
F23 C4 1.4108(11) . ?
F24 C2 1.4008(12) . ?
O14 C13 1.3254(13) . ?
O14 C15 1.4621(12) . ?
O17 C13 1.2000(13) . ?
O19 C18 1.3227(15) . ?
O19 C20 1.4577(16) . ?
O22 C18 1.1985(15) . ?
N6 C1 1.2808(15) . ?
N6 C5 1.4111(14) . ?
C7 C8 1.3881(16) . ?
C7 C12 1.3933(15) . ?
C7 C3 1.5230(14) . ?
C13 C4 1.5329(14) . ?
C3 C4 1.5411(14) . ?
C3 C2 1.5492(14) . ?
C3 H3 1.0000 . ?
C5 C25 1.3270(16) . ?
C5 C4 1.5093(15) . ?
C2 C1 1.5275(16) . ?
C2 C18 1.5383(15) . ?
C12 C11 1.3890(16) . ?
C12 H12 0.9500 . ?
C1 C26 1.5047(16) . ?
C8 C9 1.3899(17) . ?
C8 H8 0.9500 . ?
C15 C16 1.5010(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C25 H25A 0.9500 . ?
C25 H25B 0.9500 . ?
C11 C10 1.385(2) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C10 C9 1.380(2) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C20 C21 1.500(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C13 O14 C15 115.75(8) . . ?
C18 O19 C20 116.32(11) . . ?
C1 N6 C5 121.89(10) . . ?
C8 C7 C12 118.87(10) . . ?
C8 C7 C3 118.21(10) . . ?
C12 C7 C3 122.91(10) . . ?
O17 C13 O14 125.48(10) . . ?
O17 C13 C4 122.28(9) . . ?
O14 C13 C4 112.18(8) . . ?
C7 C3 C4 114.40(8) . . ?
C7 C3 C2 113.84(8) . . ?
C4 C3 C2 108.37(8) . . ?
C7 C3 H3 106.6 . . ?
C4 C3 H3 106.6 . . ?
C2 C3 H3 106.6 . . ?
C25 C5 N6 118.47(10) . . ?
C25 C5 C4 123.94(10) . . ?
N6 C5 C4 117.10(9) . . ?
F24 C2 C1 106.44(9) . . ?
F24 C2 C18 105.81(8) . . ?
C1 C2 C18 113.31(9) . . ?
F24 C2 C3 108.05(8) . . ?
C1 C2 C3 114.82(9) . . ?
C18 C2 C3 107.91(9) . . ?
F23 C4 C5 105.31(8) . . ?
F23 C4 C13 105.01(8) . . ?
C5 C4 C13 116.32(9) . . ?
F23 C4 C3 105.35(8) . . ?
C5 C4 C3 112.67(8) . . ?
C13 C4 C3 111.07(8) . . ?
C11 C12 C7 120.34(11) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N6 C1 C26 118.29(11) . . ?
N6 C1 C2 124.45(10) . . ?
C26 C1 C2 117.20(10) . . ?
O22 C18 O19 126.89(11) . . ?
O22 C18 C2 122.70(11) . . ?
O19 C18 C2 110.32(10) . . ?
C7 C8 C9 120.56(11) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
O14 C15 C16 107.03(9) . . ?
O14 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O14 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.6 . . ?
C5 C25 H25A 120.0 . . ?
C5 C25 H25B 120.0 . . ?
H25A C25 H25B 120.0 . . ?
C10 C11 C12 120.32(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C10 C11 119.60(11) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C9 C8 120.31(12) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C1 C26 H26A 109.5 . . ?
C1 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C1 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O19 C20 C21 106.47(14) . . ?
O19 C20 H20A 110.4 . . ?
C21 C20 H20A 110.4 . . ?
O19 C20 H20B 110.4 . . ?
C21 C20 H20B 110.4 . . ?
H20A C20 H20B 108.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
C15 O14 C13 O17 -3.50(15) . . . . ?
C15 O14 C13 C4 173.88(8) . . . . ?
C8 C7 C3 C4 -119.14(11) . . . . ?
C12 C7 C3 C4 62.32(13) . . . . ?
C8 C7 C3 C2 115.50(11) . . . . ?
C12 C7 C3 C2 -63.05(13) . . . . ?
C1 N6 C5 C25 -173.66(11) . . . . ?
C1 N6 C5 C4 14.07(14) . . . . ?
C7 C3 C2 F24 -146.75(9) . . . . ?
C4 C3 C2 F24 84.74(10) . . . . ?
C7 C3 C2 C1 94.66(11) . . . . ?
C4 C3 C2 C1 -33.85(12) . . . . ?
C7 C3 C2 C18 -32.76(12) . . . . ?
C4 C3 C2 C18 -161.27(9) . . . . ?
C25 C5 C4 F23 -101.36(12) . . . . ?
N6 C5 C4 F23 70.45(10) . . . . ?
C25 C5 C4 C13 14.43(15) . . . . ?
N6 C5 C4 C13 -173.76(8) . . . . ?
C25 C5 C4 C3 144.32(11) . . . . ?
N6 C5 C4 C3 -43.87(12) . . . . ?
O17 C13 C4 F23 -13.24(13) . . . . ?
O14 C13 C4 F23 169.28(8) . . . . ?
O17 C13 C4 C5 -129.20(10) . . . . ?
O14 C13 C4 C5 53.32(12) . . . . ?
O17 C13 C4 C3 100.15(11) . . . . ?
O14 C13 C4 C3 -77.33(11) . . . . ?
C7 C3 C4 F23 169.02(8) . . . . ?
C2 C3 C4 F23 -62.79(10) . . . . ?
C7 C3 C4 C5 -76.68(11) . . . . ?
C2 C3 C4 C5 51.51(11) . . . . ?
C7 C3 C4 C13 55.84(11) . . . . ?
C2 C3 C4 C13 -175.97(8) . . . . ?
C8 C7 C12 C11 0.25(16) . . . . ?
C3 C7 C12 C11 178.78(10) . . . . ?
C5 N6 C1 C26 -172.13(11) . . . . ?
C5 N6 C1 C2 5.11(16) . . . . ?
F24 C2 C1 N6 -113.06(12) . . . . ?
C18 C2 C1 N6 131.06(11) . . . . ?
C3 C2 C1 N6 6.44(15) . . . . ?
F24 C2 C1 C26 64.21(13) . . . . ?
C18 C2 C1 C26 -51.67(14) . . . . ?
C3 C2 C1 C26 -176.29(10) . . . . ?
C20 O19 C18 O22 5.93(18) . . . . ?
C20 O19 C18 C2 -170.72(10) . . . . ?
F24 C2 C18 O22 38.83(14) . . . . ?
C1 C2 C18 O22 155.08(11) . . . . ?
C3 C2 C18 O22 -76.64(13) . . . . ?
F24 C2 C18 O19 -144.35(9) . . . . ?
C1 C2 C18 O19 -28.11(12) . . . . ?
C3 C2 C18 O19 100.18(10) . . . . ?
C12 C7 C8 C9 -0.43(18) . . . . ?
C3 C7 C8 C9 -179.03(11) . . . . ?
C13 O14 C15 C16 -171.48(9) . . . . ?
C7 C12 C11 C10 -0.02(18) . . . . ?
C12 C11 C10 C9 0.0(2) . . . . ?
C11 C10 C9 C8 -0.1(2) . . . . ?
C7 C8 C9 C10 0.4(2) . . . . ?
C18 O19 C20 C21 178.18(12) . . . . ?

_refine_diff_density_max         0.382
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_mk_186_b
_database_code_depnum_ccdc_archive 'CCDC 2395308'
loop_
_audit_author_name
_audit_author_address
'Anatoly Mishnev'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-11-01 deposited with the CCDC.	2025-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 F2 N O4'
_chemical_formula_sum            'C25 H25 F2 N O4'
_chemical_formula_weight         441.46

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   12.5465(5)
_cell_length_b                   8.4111(4)
_cell_length_c                   20.7394(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.1132(19)
_cell_angle_gamma                90
_cell_volume                     2183.00(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13615
_cell_measurement_theta_min      3.5190
_cell_measurement_theta_max      75.9080

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.852
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.93a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20862
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.532
_diffrn_reflns_theta_max         76.439
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4331
_reflns_number_gt                3903
_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       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.93a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0420P)²+0.8587P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00098(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4331
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0890
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
F20 F 0.79521(5) 0.04110(8) 0.15646(3) 0.02472(17) Uani 1 1 d . . . . .
F21 F 0.81125(6) -0.03899(8) 0.28444(3) 0.02648(17) Uani 1 1 d . . . . .
O28 O 0.67010(7) -0.22708(10) 0.04694(4) 0.0262(2) Uani 1 1 d . . . . .
O26 O 0.71897(8) -0.26381(12) 0.34995(4) 0.0348(2) Uani 1 1 d . . . . .
O23 O 0.82247(7) -0.44438(10) 0.30373(4) 0.0280(2) Uani 1 1 d . . . . .
O31 O 0.62109(8) 0.01328(11) 0.08106(5) 0.0401(3) Uani 1 1 d . . . . .
C5 C 0.87092(9) -0.19557(13) 0.12356(5) 0.0201(2) Uani 1 1 d . . . . .
N6 N 0.94505(7) -0.22736(12) 0.17607(4) 0.0213(2) Uani 1 1 d . . . . .
C7 C 0.66327(9) -0.34490(13) 0.18668(5) 0.0184(2) Uani 1 1 d . . . . .
C11 C 0.49700(10) -0.49153(16) 0.18429(6) 0.0272(3) Uani 1 1 d . . . . .
H11 H 0.422982 -0.494938 0.191148 0.033 Uiso 1 1 calc R U . . .
C27 C 0.67800(9) -0.10075(14) 0.08496(5) 0.0222(2) Uani 1 1 d . . . . .
C24 C 0.80008(11) -0.56480(17) 0.35192(7) 0.0364(3) Uani 1 1 d . . . . .
H24A H 0.794582 -0.513044 0.394429 0.044 Uiso 1 1 calc R U . . .
H24B H 0.859785 -0.641905 0.356161 0.044 Uiso 1 1 calc R U . . .
C12 C 0.55476(9) -0.35254(14) 0.19691(5) 0.0227(2) Uani 1 1 d . . . . .
H12 H 0.519890 -0.261724 0.212693 0.027 Uiso 1 1 calc R U . . .
C2 C 0.80855(9) -0.19014(13) 0.25568(5) 0.0197(2) Uani 1 1 d . . . . .
C29 C 0.58237(10) -0.22721(17) -0.00377(6) 0.0296(3) Uani 1 1 d . . . . .
H29A H 0.600381 -0.298996 -0.039225 0.035 Uiso 1 1 calc R U . . .
H29B H 0.572882 -0.118698 -0.021771 0.035 Uiso 1 1 calc R U . . .
C8 C 0.71281(9) -0.48009(14) 0.16394(5) 0.0218(2) Uani 1 1 d . . . . .
H8 H 0.786717 -0.477176 0.156750 0.026 Uiso 1 1 calc R U . . .
C4 C 0.76784(9) -0.11659(13) 0.13904(5) 0.0194(2) Uani 1 1 d . . . . .
C3 C 0.72079(8) -0.18783(13) 0.19946(5) 0.0183(2) Uani 1 1 d . . . . .
H3 H 0.665370 -0.110869 0.212297 0.022 Uiso 1 1 calc R U . . .
C13 C 0.90089(9) -0.21352(14) 0.06291(5) 0.0224(2) Uani 1 1 d . . . . .
H13 H 0.850531 -0.180096 0.029238 0.027 Uiso 1 1 calc R U . . .
C14 C 1.00159(9) -0.27823(14) 0.04237(5) 0.0217(2) Uani 1 1 d . . . . .
C9 C 0.65515(10) -0.61862(14) 0.15176(6) 0.0256(3) Uani 1 1 d . . . . .
H9 H 0.689798 -0.710133 0.136419 0.031 Uiso 1 1 calc R U . . .
C17 C 1.19037(10) -0.39605(16) -0.00379(6) 0.0289(3) Uani 1 1 d . . . . .
H17 H 1.254446 -0.436108 -0.019439 0.035 Uiso 1 1 calc R U . . .
C18 C 1.15498(10) -0.45288(15) 0.05356(6) 0.0280(3) Uani 1 1 d . . . . .
H18 H 1.194919 -0.532110 0.077317 0.034 Uiso 1 1 calc R U . . .
C16 C 1.13192(10) -0.28051(16) -0.03825(6) 0.0314(3) Uani 1 1 d . . . . .
H16 H 1.156448 -0.240357 -0.077361 0.038 Uiso 1 1 calc R U . . .
C19 C 1.06139(10) -0.39455(14) 0.07650(5) 0.0249(3) Uani 1 1 d . . . . .
H19 H 1.037779 -0.434327 0.115907 0.030 Uiso 1 1 calc R U . . .
C15 C 1.03793(10) -0.22333(16) -0.01594(6) 0.0275(3) Uani 1 1 d . . . . .
H15 H 0.997548 -0.145889 -0.040456 0.033 Uiso 1 1 calc R U . . .
C1 C 0.92096(9) -0.22020(14) 0.23491(5) 0.0212(2) Uani 1 1 d . . . . .
C10 C 0.54701(10) -0.62451(15) 0.16183(6) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.507647 -0.719614 0.153303 0.032 Uiso 1 1 calc R U . . .
C22 C 0.77711(9) -0.30344(14) 0.30927(5) 0.0226(2) Uani 1 1 d . . . . .
C32 C 1.00939(10) -0.23108(18) 0.28736(6) 0.0321(3) Uani 1 1 d . . . . .
H32A H 0.979403 -0.223943 0.329611 0.048 Uiso 0.5 1 calc R U P . .
H32B H 1.046667 -0.332800 0.283971 0.048 Uiso 0.5 1 calc R U P . .
H32C H 1.059882 -0.143607 0.282758 0.048 Uiso 0.5 1 calc R U P . .
H32D H 1.077898 -0.242957 0.267949 0.048 Uiso 0.5 1 calc R U P . .
H32E H 1.010635 -0.134100 0.313589 0.048 Uiso 0.5 1 calc R U P . .
H32F H 0.997419 -0.323293 0.314802 0.048 Uiso 0.5 1 calc R U P . .
C30 C 0.48093(11) -0.28070(19) 0.02243(7) 0.0383(3) Uani 1 1 d . . . . .
H30A H 0.424940 -0.288582 -0.012881 0.058 Uiso 1 1 calc R U . . .
H30B H 0.459321 -0.203738 0.054489 0.058 Uiso 1 1 calc R U . . .
H30C H 0.491757 -0.384984 0.042935 0.058 Uiso 1 1 calc R U . . .
C25 C 0.69869(13) -0.6505(2) 0.33316(8) 0.0492(4) Uani 1 1 d . . . . .
H25A H 0.702528 -0.696629 0.289996 0.074 Uiso 1 1 calc R U . . .
H25B H 0.638690 -0.575823 0.332723 0.074 Uiso 1 1 calc R U . . .
H25C H 0.688150 -0.735443 0.364413 0.074 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
F20 C4 1.4106(12) . ?
F21 C2 1.4037(12) . ?
O28 C27 1.3226(14) . ?
O28 C29 1.4670(14) . ?
O26 C22 1.2013(14) . ?
O23 C22 1.3236(15) . ?
O23 C24 1.4643(15) . ?
O31 C27 1.1950(15) . ?
C5 C13 1.3471(16) . ?
C5 N6 1.4061(14) . ?
C5 C4 1.5087(15) . ?
N6 C1 1.2795(15) . ?
C7 C8 1.3942(16) . ?
C7 C12 1.3943(15) . ?
C7 C3 1.5196(15) . ?
C11 C10 1.3797(18) . ?
C11 C12 1.3904(17) . ?
C11 H11 0.9500 . ?
C27 C4 1.5378(15) . ?
C24 C25 1.489(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C12 H12 0.9500 . ?
C2 C1 1.5251(15) . ?
C2 C22 1.5369(16) . ?
C2 C3 1.5454(15) . ?
C29 C30 1.4889(18) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C8 C9 1.3852(17) . ?
C8 H8 0.9500 . ?
C4 C3 1.5439(15) . ?
C3 H3 1.0000 . ?
C13 C14 1.4667(16) . ?
C13 H13 0.9500 . ?
C14 C19 1.3946(17) . ?
C14 C15 1.4009(16) . ?
C9 C10 1.3884(17) . ?
C9 H9 0.9500 . ?
C17 C18 1.3844(17) . ?
C17 C16 1.3848(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3877(17) . ?
C18 H18 0.9500 . ?
C16 C15 1.3836(18) . ?
C16 H16 0.9500 . ?
C19 H19 0.9500 . ?
C15 H15 0.9500 . ?
C1 C32 1.4997(16) . ?
C10 H10 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C32 H32D 0.9800 . ?
C32 H32E 0.9800 . ?
C32 H32F 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C27 O28 C29 116.63(9) . . ?
C22 O23 C24 117.09(10) . . ?
C13 C5 N6 119.24(10) . . ?
C13 C5 C4 123.29(10) . . ?
N6 C5 C4 116.65(9) . . ?
C1 N6 C5 122.78(10) . . ?
C8 C7 C12 118.54(10) . . ?
C8 C7 C3 123.39(10) . . ?
C12 C7 C3 118.05(10) . . ?
C10 C11 C12 120.12(11) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O31 C27 O28 125.85(11) . . ?
O31 C27 C4 121.46(10) . . ?
O28 C27 C4 112.63(9) . . ?
O23 C24 C25 111.01(11) . . ?
O23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
O23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C11 C12 C7 120.76(11) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
F21 C2 C1 106.00(9) . . ?
F21 C2 C22 104.70(8) . . ?
C1 C2 C22 113.08(9) . . ?
F21 C2 C3 107.66(9) . . ?
C1 C2 C3 114.35(9) . . ?
C22 C2 C3 110.34(9) . . ?
O28 C29 C30 110.83(10) . . ?
O28 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O28 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
C9 C8 C7 120.54(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
F20 C4 C5 105.77(8) . . ?
F20 C4 C27 104.93(8) . . ?
C5 C4 C27 118.53(9) . . ?
F20 C4 C3 104.90(8) . . ?
C5 C4 C3 112.66(9) . . ?
C27 C4 C3 108.82(9) . . ?
C7 C3 C4 113.60(9) . . ?
C7 C3 C2 115.11(9) . . ?
C4 C3 C2 108.91(9) . . ?
C7 C3 H3 106.2 . . ?
C4 C3 H3 106.2 . . ?
C2 C3 H3 106.2 . . ?
C5 C13 C14 128.08(11) . . ?
C5 C13 H13 116.0 . . ?
C14 C13 H13 116.0 . . ?
C19 C14 C15 118.22(11) . . ?
C19 C14 C13 123.79(10) . . ?
C15 C14 C13 117.96(11) . . ?
C8 C9 C10 120.39(11) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C18 C17 C16 119.68(11) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C19 120.26(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C15 C16 C17 120.26(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C19 C14 120.77(11) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C16 C15 C14 120.80(12) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
N6 C1 C32 118.42(10) . . ?
N6 C1 C2 124.31(10) . . ?
C32 C1 C2 117.15(10) . . ?
C11 C10 C9 119.66(11) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
O26 C22 O23 126.59(11) . . ?
O26 C22 C2 122.42(11) . . ?
O23 C22 C2 110.99(9) . . ?
C1 C32 H32A 109.5 . . ?
C1 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C1 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H32D C32 H32E 109.5 . . ?
H32D C32 H32F 109.5 . . ?
H32E C32 H32F 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037

