# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dp116_0m
_database_code_depnum_ccdc_archive 'CCDC 2253122'
loop_
_audit_author_name
_audit_author_address
'Daria Gerasimova'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center
Russia
;
_audit_update_record             
;
2023-03-31 deposited with the CCDC.	2023-07-24 downloaded from the CCDC.
;
_audit_creation_date             2023-03-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C2 F3 O2, C3 H5 N2 O'
_chemical_formula_sum            'C5 H5 F3 N2 O3'
_chemical_formula_weight         198.11
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.243(2)
_cell_length_b                   8.488(3)
_cell_length_c                   11.355(3)
_cell_angle_alpha                80.218(8)
_cell_angle_beta                 73.432(8)
_cell_angle_gamma                78.498(8)
_cell_volume                     740.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3946
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      26.55
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5961
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1535 before and 0.0844 after correction.
The Ratio of minimum to maximum transmission is 0.7991.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.776
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             400
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4.00 0.00 1.00 0.1390
-4.00 -1.00 -2.00 0.1270
-3.00 -1.00 3.00 0.0780
-2.00 -1.00 -3.00 0.0960
-2.00 -2.00 1.00 0.0570
-1.00 -1.00 -4.00 0.0510
-1.00 -1.00 0.00 0.0550
1.00 1.00 4.00 0.0070
1.00 1.00 -1.00 0.0100
1.00 -1.00 1.00 0.1930
4.00 1.00 2.00 0.1270

_exptl_crystal_size_max          0.451
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1088
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20109
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.885
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1973
_reflns_number_total             2895
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         2895
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0733P)²+0.5423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1299
_refine_ls_wR_factor_ref         0.1512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1A-H1A = O1B-H1B
 0.84 with sigma of 0.02
 N1A-H1AA = N2A-H2A = N1B-H1BA = N2B-H2B
 0.88 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C3B(H3B), C2A(H2AA), C2B(H2BA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
F1B F 0.2653(2) 0.4043(2) 0.93415(17) 0.0311(5) Uani 1 1 d . . . . .
F1A F -0.1053(3) 0.8791(3) 0.12586(17) 0.0331(5) Uani 1 1 d . . . . .
F3A F 0.0852(3) 0.6701(2) 0.07705(17) 0.0330(5) Uani 1 1 d . . . . .
F2A F 0.1630(3) 0.8941(2) 0.08609(18) 0.0341(5) Uani 1 1 d . . . . .
F2B F 0.3815(3) 0.1654(3) 0.99256(17) 0.0387(6) Uani 1 1 d . . . . .
F3B F 0.5312(3) 0.3578(3) 0.93222(19) 0.0402(6) Uani 1 1 d . . . . .
O2A O 0.1517(3) 0.6305(3) 0.30025(19) 0.0230(5) Uani 1 1 d . . . . .
O2B O 0.5686(3) 0.1320(3) 0.7550(2) 0.0239(6) Uani 1 1 d . . . . .
O1B O 0.6823(3) 0.0675(3) 0.5428(2) 0.0218(5) Uani 1 1 d D . . . .
O1A O 0.1897(3) 0.5568(3) 0.5095(2) 0.0234(5) Uani 1 1 d D . . . .
O3A O -0.0652(3) 0.8330(3) 0.3521(2) 0.0284(6) Uani 1 1 d . . . . .
O3B O 0.3881(3) 0.3492(3) 0.7024(2) 0.0269(6) Uani 1 1 d . . . . .
N1B N 0.4935(3) 0.2658(3) 0.4504(2) 0.0199(6) Uani 1 1 d D . . . .
N2A N 0.1163(4) 0.6013(3) 0.7147(2) 0.0194(6) Uani 1 1 d D . . . .
N2B N 0.6732(4) 0.0917(3) 0.3387(2) 0.0207(6) Uani 1 1 d D . . . .
N1A N -0.0361(3) 0.7566(3) 0.6011(2) 0.0194(6) Uani 1 1 d D . . . .
C1A C 0.0950(4) 0.6352(4) 0.6011(3) 0.0175(7) Uani 1 1 d . . . . .
C1B C 0.6192(4) 0.1375(4) 0.4528(3) 0.0186(7) Uani 1 1 d . . . . .
C5B C 0.4575(4) 0.2576(4) 0.7754(3) 0.0198(7) Uani 1 1 d . . . . .
C3A C -0.1003(4) 0.8016(4) 0.7210(3) 0.0212(7) Uani 1 1 d . . . . .
H3A H -0.193218 0.884942 0.747534 0.025 Uiso 1 1 calc R U . . .
C3B C 0.4690(4) 0.3011(4) 0.3319(3) 0.0207(7) Uani 1 1 d . . . . .
H3B H 0.388330 0.385865 0.305128 0.025 Uiso 1 1 calc R U . . .
C2A C -0.0059(4) 0.7049(4) 0.7907(3) 0.0211(7) Uani 1 1 d . . . . .
H2AA H -0.019520 0.706475 0.876444 0.025 Uiso 1 1 calc R U . . .
C4A C 0.0468(4) 0.7972(4) 0.1405(3) 0.0221(7) Uani 1 1 d . . . . .
C5A C 0.0420(4) 0.7499(4) 0.2778(3) 0.0198(7) Uani 1 1 d . . . . .
C2B C 0.5806(4) 0.1932(4) 0.2623(3) 0.0212(7) Uani 1 1 d . . . . .
H2BA H 0.593769 0.187252 0.177233 0.025 Uiso 1 1 calc R U . . .
C4B C 0.4083(4) 0.2963(4) 0.9105(3) 0.0230(8) Uani 1 1 d . . . . .
H1AA H -0.066(4) 0.790(4) 0.533(2) 0.025(10) Uiso 1 1 d D . . . .
H1A H 0.170(6) 0.590(5) 0.437(2) 0.058(14) Uiso 1 1 d D . . . .
H2A H 0.196(4) 0.523(3) 0.735(3) 0.030(10) Uiso 1 1 d D . . . .
H1BA H 0.439(4) 0.313(4) 0.516(2) 0.033(10) Uiso 1 1 d D . . . .
H1B H 0.634(5) 0.091(5) 0.618(2) 0.061(14) Uiso 1 1 d D . . . .
H2B H 0.760(4) 0.015(4) 0.319(4) 0.049(13) Uiso 1 1 d 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
F1B C4B 1.332(4) . ?
F1A C4A 1.347(4) . ?
F3A C4A 1.334(4) . ?
F2A C4A 1.334(4) . ?
F2B C4B 1.334(4) . ?
F3B C4B 1.326(4) . ?
O2A C5A 1.260(4) . ?
O2B C5B 1.266(4) . ?
O1B C1B 1.281(4) . ?
O1B H1B 0.874(19) . ?
O1A C1A 1.303(4) . ?
O1A H1A 0.872(19) . ?
O3A C5A 1.232(4) . ?
O3B C5B 1.222(4) . ?
N1B C1B 1.348(4) . ?
N1B C3B 1.391(4) . ?
N1B H1BA 0.871(18) . ?
N2A C1A 1.327(4) . ?
N2A C2A 1.393(4) . ?
N2A H2A 0.885(18) . ?
N2B C1B 1.343(4) . ?
N2B C2B 1.392(4) . ?
N2B H2B 0.871(19) . ?
N1A C1A 1.337(4) . ?
N1A C3A 1.401(4) . ?
N1A H1AA 0.860(18) . ?
C5B C4B 1.546(4) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.335(5) . ?
C3B H3B 0.9500 . ?
C3B C2B 1.344(5) . ?
C2A H2AA 0.9500 . ?
C4A C5A 1.535(5) . ?
C2B H2BA 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1B O1B H1B 121(3) . . ?
C1A O1A H1A 117(3) . . ?
C1B N1B C3B 109.2(3) . . ?
C1B N1B H1BA 122(2) . . ?
C3B N1B H1BA 129(2) . . ?
C1A N2A C2A 108.8(3) . . ?
C1A N2A H2A 123(2) . . ?
C2A N2A H2A 128(2) . . ?
C1B N2B C2B 109.5(3) . . ?
C1B N2B H2B 121(3) . . ?
C2B N2B H2B 129(3) . . ?
C1A N1A C3A 108.5(3) . . ?
C1A N1A H1AA 118(2) . . ?
C3A N1A H1AA 133(2) . . ?
O1A C1A N2A 123.0(3) . . ?
O1A C1A N1A 128.6(3) . . ?
N2A C1A N1A 108.4(3) . . ?
O1B C1B N1B 129.3(3) . . ?
O1B C1B N2B 123.7(3) . . ?
N2B C1B N1B 107.0(3) . . ?
O2B C5B C4B 113.9(3) . . ?
O3B C5B O2B 128.2(3) . . ?
O3B C5B C4B 117.9(3) . . ?
N1A C3A H3A 126.6 . . ?
C2A C3A N1A 106.8(3) . . ?
C2A C3A H3A 126.6 . . ?
N1B C3B H3B 126.3 . . ?
C2B C3B N1B 107.3(3) . . ?
C2B C3B H3B 126.3 . . ?
N2A C2A H2AA 126.2 . . ?
C3A C2A N2A 107.5(3) . . ?
C3A C2A H2AA 126.2 . . ?
F1A C4A C5A 111.4(3) . . ?
F3A C4A F1A 107.0(3) . . ?
F3A C4A F2A 107.5(3) . . ?
F3A C4A C5A 113.2(3) . . ?
F2A C4A F1A 106.8(3) . . ?
F2A C4A C5A 110.6(3) . . ?
O2A C5A C4A 115.0(3) . . ?
O3A C5A O2A 128.0(3) . . ?
O3A C5A C4A 117.0(3) . . ?
N2B C2B H2BA 126.5 . . ?
C3B C2B N2B 106.9(3) . . ?
C3B C2B H2BA 126.5 . . ?
F1B C4B F2B 107.1(3) . . ?
F1B C4B C5B 111.3(3) . . ?
F2B C4B C5B 112.5(3) . . ?
F3B C4B F1B 107.4(3) . . ?
F3B C4B F2B 107.5(3) . . ?
F3B C4B C5B 110.8(3) . . ?

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
F1A C4A C5A O2A 156.6(3) . . . . ?
F1A C4A C5A O3A -24.3(4) . . . . ?
F3A C4A C5A O2A 36.0(4) . . . . ?
F3A C4A C5A O3A -144.9(3) . . . . ?
F2A C4A C5A O2A -84.7(3) . . . . ?
F2A C4A C5A O3A 94.4(3) . . . . ?
O2B C5B C4B F1B -165.4(3) . . . . ?
O2B C5B C4B F2B -45.2(4) . . . . ?
O2B C5B C4B F3B 75.1(4) . . . . ?
O3B C5B C4B F1B 15.1(4) . . . . ?
O3B C5B C4B F2B 135.3(3) . . . . ?
O3B C5B C4B F3B -104.4(3) . . . . ?
N1B C3B C2B N2B 0.1(4) . . . . ?
N1A C3A C2A N2A 0.3(4) . . . . ?
C1A N2A C2A C3A -0.2(4) . . . . ?
C1A N1A C3A C2A -0.2(4) . . . . ?
C1B N1B C3B C2B 0.1(4) . . . . ?
C1B N2B C2B C3B -0.2(4) . . . . ?
C3A N1A C1A O1A 179.4(3) . . . . ?
C3A N1A C1A N2A 0.1(4) . . . . ?
C3B N1B C1B O1B 179.3(3) . . . . ?
C3B N1B C1B N2B -0.2(4) . . . . ?
C2A N2A C1A O1A -179.3(3) . . . . ?
C2A N2A C1A N1A 0.0(4) . . . . ?
C2B N2B C1B O1B -179.2(3) . . . . ?
C2B N2B C1B N1B 0.3(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
