# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_database_code_depnum_ccdc_archive 'CCDC 2039146'
loop_
_audit_author_name
_audit_author_address
'Wei Zeng'
;South China University of Technology
China
;
_audit_update_record             
;
2020-10-18 deposited with the CCDC.	2021-03-31 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         'C21 H15 F3 N2 O'
_chemical_formula_sum            'C21 H15 F3 N2 O'
_chemical_formula_weight         368.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   13.1916(8)
_cell_length_b                   8.4604(4)
_cell_length_c                   15.8473(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.037(6)
_cell_angle_gamma                90
_cell_volume                     1715.84(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    3475
_cell_measurement_theta_min      2.3370
_cell_measurement_theta_max      28.7910

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.88482
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8441
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         29.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4038
_reflns_number_gt                3266
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²+0.3000P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4038
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1622
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1 O 0.54237(9) 0.67925(13) 0.05891(7) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.70809(10) 0.80291(15) 0.08902(9) 0.0177(3) Uani 1 1 d . . . . .
N3 N 0.85322(11) 0.63962(17) 0.09936(9) 0.0202(3) Uani 1 1 d . . . . .
C4 C 0.38234(13) 0.92404(19) 0.08004(10) 0.0191(4) Uani 1 1 d . . . . .
H4 H 0.387889 0.857687 0.034586 0.023 Uiso 1 1 calc R U . . .
C5 C 0.28501(13) 0.9631(2) 0.09113(11) 0.0208(4) Uani 1 1 d . . . . .
H5 H 0.225444 0.922856 0.053233 0.025 Uiso 1 1 calc R U . . .
C6 C 0.69491(13) 1.18953(19) 0.17774(10) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.644111 1.251104 0.193576 0.022 Uiso 1 1 calc R U . . .
C7 C 0.57661(12) 0.94343(19) 0.12362(10) 0.0165(3) Uani 1 1 d . . . . .
C8 C 0.79458(13) 1.2484(2) 0.18523(11) 0.0201(4) Uani 1 1 d . . . . .
H8 H 0.810120 1.350894 0.205501 0.024 Uiso 1 1 calc R U . . .
C9 C 0.90079(14) 0.5222(2) 0.06670(12) 0.0245(4) Uani 1 1 d . . . . .
H9 H 0.967464 0.492495 0.097286 0.029 Uiso 1 1 calc R U . . .
C10 C 0.60291(12) 0.80594(19) 0.08904(10) 0.0171(3) Uani 1 1 d . . . . .
F11 F 0.10501(10) 1.1480(2) 0.09351(8) 0.0554(4) Uani 1 1 d . . . . .
C12 C 0.75884(13) 0.68153(18) 0.05297(10) 0.0179(3) Uani 1 1 d . . . . .
C13 C 0.46213(13) 1.08090(19) 0.20523(11) 0.0192(4) Uani 1 1 d . . . . .
H13 H 0.521429 1.119324 0.244223 0.023 Uiso 1 1 calc R U . . .
F14 F 0.16862(10) 1.22558(19) 0.22215(11) 0.0621(5) Uani 1 1 d . . . . .
F15 F 0.12202(11) 0.98800(16) 0.19896(13) 0.0656(5) Uani 1 1 d . . . . .
C16 C 0.87219(13) 1.1570(2) 0.16293(11) 0.0207(4) Uani 1 1 d . . . . .
H16 H 0.938385 1.199892 0.168451 0.025 Uiso 1 1 calc R U . . .
C17 C 0.36437(13) 1.1209(2) 0.21588(11) 0.0212(4) Uani 1 1 d . . . . .
H17 H 0.358208 1.186948 0.261276 0.025 Uiso 1 1 calc R U . . .
C18 C 0.75200(12) 0.94581(18) 0.12411(10) 0.0165(3) Uani 1 1 d . . . . .
C19 C 0.70961(14) 0.6135(2) -0.02640(11) 0.0234(4) Uani 1 1 d . . . . .
H19 H 0.644875 0.649735 -0.057833 0.028 Uiso 1 1 calc R U . . .
C20 C 0.47320(12) 0.98329(18) 0.13655(10) 0.0165(3) Uani 1 1 d . . . . .
C21 C 0.67153(12) 1.03542(19) 0.14589(10) 0.0166(3) Uani 1 1 d . . . . .
C22 C 0.75948(15) 0.4911(2) -0.05703(12) 0.0283(4) Uani 1 1 d . . . . .
H22 H 0.728147 0.441172 -0.109122 0.034 Uiso 1 1 calc R U . . .
C23 C 0.85266(13) 1.00339(19) 0.13271(11) 0.0191(3) Uani 1 1 d . . . . .
H23 H 0.904649 0.941658 0.118812 0.023 Uiso 1 1 calc R U . . .
C24 C 0.27542(13) 1.0623(2) 0.15874(11) 0.0204(4) Uani 1 1 d . . . . .
C25 C 0.55674(15) 0.5477(2) 0.11829(12) 0.0293(4) Uani 1 1 d . . . . .
H25A H 0.538922 0.451291 0.086146 0.044 Uiso 1 1 calc R U . . .
H25B H 0.512482 0.560602 0.157777 0.044 Uiso 1 1 calc R U . . .
H25C H 0.628397 0.543419 0.150534 0.044 Uiso 1 1 calc R U . . .
C26 C 0.85677(15) 0.4433(2) -0.00928(13) 0.0280(4) Uani 1 1 d . . . . .
H26 H 0.891631 0.359874 -0.028073 0.034 Uiso 1 1 calc R U . . .
C27 C 0.16901(14) 1.1052(2) 0.16798(12) 0.0250(4) Uani 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 C10 1.3527(19) . ?
O1 C25 1.440(2) . ?
N2 C10 1.388(2) . ?
N2 C18 1.396(2) . ?
N2 C12 1.419(2) . ?
N3 C12 1.331(2) . ?
N3 C9 1.344(2) . ?
C4 C5 1.378(2) . ?
C4 C20 1.403(2) . ?
C5 C24 1.391(2) . ?
C6 C8 1.384(2) . ?
C6 C21 1.405(2) . ?
C7 C10 1.366(2) . ?
C7 C21 1.444(2) . ?
C7 C20 1.467(2) . ?
C8 C16 1.395(2) . ?
C9 C26 1.376(3) . ?
F11 C27 1.324(2) . ?
C12 C19 1.392(2) . ?
C13 C17 1.383(2) . ?
C13 C20 1.402(2) . ?
F14 C27 1.333(2) . ?
F15 C27 1.325(2) . ?
C16 C23 1.387(2) . ?
C17 C24 1.388(2) . ?
C18 C23 1.390(2) . ?
C18 C21 1.414(2) . ?
C19 C22 1.377(3) . ?
C22 C26 1.383(3) . ?
C24 C27 1.491(2) . ?

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
C10 O1 C25 114.14(12) . . ?
C10 N2 C18 107.59(13) . . ?
C10 N2 C12 125.64(13) . . ?
C18 N2 C12 126.58(13) . . ?
C12 N3 C9 116.47(15) . . ?
C5 C4 C20 120.74(15) . . ?
C4 C5 C24 120.31(15) . . ?
C8 C6 C21 119.08(15) . . ?
C10 C7 C21 105.52(14) . . ?
C10 C7 C20 125.95(14) . . ?
C21 C7 C20 128.52(14) . . ?
C6 C8 C16 121.26(15) . . ?
N3 C9 C26 123.93(17) . . ?
O1 C10 C7 129.10(15) . . ?
O1 C10 N2 119.34(14) . . ?
C7 C10 N2 111.53(14) . . ?
N3 C12 C19 123.89(15) . . ?
N3 C12 N2 116.08(14) . . ?
C19 C12 N2 120.03(15) . . ?
C17 C13 C20 120.99(15) . . ?
C23 C16 C8 121.37(15) . . ?
C13 C17 C24 119.93(15) . . ?
C23 C18 N2 129.55(14) . . ?
C23 C18 C21 122.97(14) . . ?
N2 C18 C21 107.33(13) . . ?
C22 C19 C12 118.12(17) . . ?
C13 C20 C4 118.18(15) . . ?
C13 C20 C7 121.29(14) . . ?
C4 C20 C7 120.53(14) . . ?
C6 C21 C18 118.23(14) . . ?
C6 C21 C7 133.62(15) . . ?
C18 C21 C7 108.02(14) . . ?
C19 C22 C26 119.09(17) . . ?
C16 C23 C18 117.08(15) . . ?
C17 C24 C5 119.84(15) . . ?
C17 C24 C27 121.07(15) . . ?
C5 C24 C27 119.09(15) . . ?
C9 C26 C22 118.41(17) . . ?
F11 C27 F15 106.29(16) . . ?
F11 C27 F14 105.29(15) . . ?
F15 C27 F14 104.95(16) . . ?
F11 C27 C24 113.01(14) . . ?
F15 C27 C24 112.98(15) . . ?
F14 C27 C24 113.58(15) . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.063



