# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_yzp039
_database_code_depnum_ccdc_archive 'CCDC 2191985'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2022-07-22 deposited with the CCDC.	2024-11-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 F3 N2 O2'
_chemical_formula_sum            'C19 H17 F3 N2 O2'
_chemical_formula_weight         362.34

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'
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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   32.3188(11)
_cell_length_b                   4.4791(2)
_cell_length_c                   23.8716(8)
_cell_angle_alpha                90
_cell_angle_beta                 107.0298(13)
_cell_angle_gamma                90
_cell_volume                     3304.1(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9353
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      74.46

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.630
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    1.009
_shelx_estimated_absorpt_T_min   0.569
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5344
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10334
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.860
_diffrn_reflns_theta_max         74.453
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             3188
_reflns_number_gt                2990
_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       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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)+(0.0500P)²+4.3485P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1358
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
F1 F 0.57497(4) 0.8818(3) 0.70172(6) 0.0499(4) Uani 1 1 d . . . . .
F2 F 0.57048(4) 0.9547(4) 0.61152(6) 0.0514(4) Uani 1 1 d . . . . .
F3 F 0.59838(4) 0.5523(3) 0.65442(7) 0.0525(4) Uani 1 1 d . . . . .
O1 O 0.42983(4) 0.5248(4) 0.50214(5) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.27461(5) 0.7833(3) 0.26211(6) 0.0365(3) Uani 1 1 d D . . . .
H2O H 0.2572(9) 0.934(6) 0.2514(13) 0.051(8) Uiso 1 1 d D . . . .
N1 N 0.40168(5) 0.1784(4) 0.57886(6) 0.0262(3) Uani 1 1 d . . . . .
N2 N 0.28586(5) 0.7987(4) 0.39225(7) 0.0345(4) Uani 1 1 d . . . . .
C1 C 0.56608(6) 0.7479(5) 0.64908(8) 0.0332(4) Uani 1 1 d . . . . .
C2 C 0.52257(5) 0.6043(4) 0.63182(7) 0.0264(4) Uani 1 1 d . . . . .
C3 C 0.49524(6) 0.6356(4) 0.57479(7) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.503809 0.752632 0.546908 0.032 Uiso 1 1 calc R U . . .
C4 C 0.45573(5) 0.4947(4) 0.55962(7) 0.0245(4) Uani 1 1 d . . . . .
C5 C 0.44194(5) 0.3178(4) 0.59906(7) 0.0242(3) Uani 1 1 d . . . . .
C6 C 0.46980(6) 0.2922(4) 0.65635(7) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.461243 0.177515 0.684540 0.035 Uiso 1 1 calc R U . . .
C7 C 0.50966(6) 0.4333(4) 0.67195(8) 0.0299(4) Uani 1 1 d . . . . .
H7 H 0.528378 0.412361 0.710701 0.036 Uiso 1 1 calc R U . . .
C11 C 0.36241(8) 0.3312(6) 0.69627(9) 0.0471(6) Uani 1 1 d . . . . .
H11 H 0.354455 0.455306 0.723693 0.071 Uiso 1 1 calc R U . . .
C12 C 0.37226(6) 0.1777(5) 0.66234(8) 0.0335(4) Uani 1 1 d . . . . .
C13 C 0.38623(6) -0.0013(4) 0.61940(8) 0.0313(4) Uani 1 1 d . . . . .
H13A H 0.409643 -0.138023 0.640664 0.038 Uiso 1 1 calc R U . . .
H13B H 0.361631 -0.125101 0.596755 0.038 Uiso 1 1 calc R U . . .
C21 C 0.38568(5) 0.5067(4) 0.49531(7) 0.0254(4) Uani 1 1 d . . . . .
C22 C 0.37063(6) 0.3321(4) 0.53339(7) 0.0243(3) Uani 1 1 d . . . . .
C23 C 0.32613(6) 0.3190(4) 0.52321(7) 0.0279(4) Uani 1 1 d . . . . .
H23 H 0.314643 0.202830 0.548445 0.033 Uiso 1 1 calc R U . . .
C24 C 0.29801(6) 0.4723(5) 0.47685(8) 0.0294(4) Uani 1 1 d . . . . .
H24 H 0.267697 0.457292 0.470809 0.035 Uiso 1 1 calc R U . . .
C25 C 0.31355(6) 0.6485(4) 0.43888(7) 0.0260(4) Uani 1 1 d . . . . .
C26 C 0.35876(6) 0.6624(4) 0.44976(7) 0.0264(4) Uani 1 1 d . . . . .
H26 H 0.370655 0.780911 0.425277 0.032 Uiso 1 1 calc R U . . .
C27 C 0.23946(6) 0.7768(6) 0.38171(9) 0.0425(5) Uani 1 1 d . . . . .
H27A H 0.230702 0.566669 0.376582 0.064 Uiso 1 1 calc R U . . .
H27B H 0.224671 0.888703 0.346223 0.064 Uiso 1 1 calc R U . . .
H27C H 0.231645 0.860049 0.415198 0.064 Uiso 1 1 calc R U . . .
C28 C 0.30205(6) 1.0149(5) 0.35877(8) 0.0309(4) Uani 1 1 d . . . . .
H28A H 0.328656 1.106766 0.384699 0.037 Uiso 1 1 calc R U . . .
H28B H 0.280270 1.175292 0.345689 0.037 Uiso 1 1 calc R U . . .
C29 C 0.31216(6) 0.8862(5) 0.30577(8) 0.0318(4) Uani 1 1 d . . . . .
H29A H 0.326577 1.040885 0.288490 0.038 Uiso 1 1 calc R U . . .
H29B H 0.332619 0.717826 0.318364 0.038 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 C1 1.345(2) . ?
F2 C1 1.326(3) . ?
F3 C1 1.340(2) . ?
O1 C4 1.389(2) . ?
O1 C21 1.390(2) . ?
O2 C29 1.425(2) . ?
N1 C5 1.396(2) . ?
N1 C22 1.422(2) . ?
N1 C13 1.455(2) . ?
N2 C25 1.382(2) . ?
N2 C28 1.447(3) . ?
N2 C27 1.449(2) . ?
C1 C2 1.490(3) . ?
C2 C7 1.383(3) . ?
C2 C3 1.396(2) . ?
C3 C4 1.374(3) . ?
C4 C5 1.400(2) . ?
C5 C6 1.404(2) . ?
C6 C7 1.384(3) . ?
C11 C12 1.175(3) . ?
C12 C13 1.473(3) . ?
C21 C26 1.368(3) . ?
C21 C22 1.391(2) . ?
C22 C23 1.388(2) . ?
C23 C24 1.390(3) . ?
C24 C25 1.401(3) . ?
C25 C26 1.409(2) . ?
C28 C29 1.511(3) . ?

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
C4 O1 C21 114.27(12) . . ?
C5 N1 C22 115.17(14) . . ?
C5 N1 C13 118.97(14) . . ?
C22 N1 C13 118.22(14) . . ?
C25 N2 C28 121.14(15) . . ?
C25 N2 C27 119.99(17) . . ?
C28 N2 C27 118.20(17) . . ?
F2 C1 F3 106.64(17) . . ?
F2 C1 F1 106.52(17) . . ?
F3 C1 F1 104.79(16) . . ?
F2 C1 C2 113.20(16) . . ?
F3 C1 C2 112.95(17) . . ?
F1 C1 C2 112.12(16) . . ?
C7 C2 C3 119.88(17) . . ?
C7 C2 C1 119.94(16) . . ?
C3 C2 C1 120.17(17) . . ?
C4 C3 C2 118.98(16) . . ?
C3 C4 O1 117.41(15) . . ?
C3 C4 C5 122.48(15) . . ?
O1 C4 C5 120.08(15) . . ?
N1 C5 C4 117.98(15) . . ?
N1 C5 C6 124.54(16) . . ?
C4 C5 C6 117.48(16) . . ?
C7 C6 C5 120.37(17) . . ?
C2 C7 C6 120.80(16) . . ?
C11 C12 C13 176.8(2) . . ?
N1 C13 C12 113.38(16) . . ?
C26 C21 O1 117.09(15) . . ?
C26 C21 C22 122.94(16) . . ?
O1 C21 C22 119.97(16) . . ?
C23 C22 C21 116.88(16) . . ?
C23 C22 N1 125.22(16) . . ?
C21 C22 N1 117.89(15) . . ?
C22 C23 C24 121.39(16) . . ?
C23 C24 C25 121.24(16) . . ?
N2 C25 C24 121.69(16) . . ?
N2 C25 C26 121.27(16) . . ?
C24 C25 C26 117.04(16) . . ?
C21 C26 C25 120.51(16) . . ?
N2 C28 C29 114.14(17) . . ?
O2 C29 C28 112.92(15) . . ?

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
F2 C1 C2 C7 -166.02(17) . . . . ?
F3 C1 C2 C7 72.7(2) . . . . ?
F1 C1 C2 C7 -45.5(2) . . . . ?
F2 C1 C2 C3 15.6(3) . . . . ?
F3 C1 C2 C3 -105.7(2) . . . . ?
F1 C1 C2 C3 136.16(18) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 178.37(16) . . . . ?
C2 C3 C4 O1 -178.46(16) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C21 O1 C4 C3 -151.43(17) . . . . ?
C21 O1 C4 C5 30.7(2) . . . . ?
C22 N1 C5 C4 -29.6(2) . . . . ?
C13 N1 C5 C4 -178.66(15) . . . . ?
C22 N1 C5 C6 150.60(17) . . . . ?
C13 N1 C5 C6 1.6(3) . . . . ?
C3 C4 C5 N1 -178.45(16) . . . . ?
O1 C4 C5 N1 -0.7(2) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
O1 C4 C5 C6 179.07(16) . . . . ?
N1 C5 C6 C7 178.40(17) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C3 C2 C7 C6 -0.1(3) . . . . ?
C1 C2 C7 C6 -178.44(17) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C5 N1 C13 C12 73.3(2) . . . . ?
C22 N1 C13 C12 -74.8(2) . . . . ?
C4 O1 C21 C26 150.53(17) . . . . ?
C4 O1 C21 C22 -30.4(2) . . . . ?
C26 C21 C22 C23 0.4(3) . . . . ?
O1 C21 C22 C23 -178.60(16) . . . . ?
C26 C21 C22 N1 179.47(16) . . . . ?
O1 C21 C22 N1 0.5(2) . . . . ?
C5 N1 C22 C23 -151.15(17) . . . . ?
C13 N1 C22 C23 -1.9(3) . . . . ?
C5 N1 C22 C21 29.9(2) . . . . ?
C13 N1 C22 C21 179.13(16) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
N1 C22 C23 C24 -178.66(16) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
C28 N2 C25 C24 170.52(17) . . . . ?
C27 N2 C25 C24 0.1(3) . . . . ?
C28 N2 C25 C26 -10.5(3) . . . . ?
C27 N2 C25 C26 179.15(18) . . . . ?
C23 C24 C25 N2 179.19(17) . . . . ?
C23 C24 C25 C26 0.1(3) . . . . ?
O1 C21 C26 C25 178.14(15) . . . . ?
C22 C21 C26 C25 -0.9(3) . . . . ?
N2 C25 C26 C21 -178.47(17) . . . . ?
C24 C25 C26 C21 0.6(3) . . . . ?
C25 N2 C28 C29 92.2(2) . . . . ?
C27 N2 C28 C29 -97.3(2) . . . . ?
N2 C28 C29 O2 66.1(2) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.057



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF, EA, Hexane'
