# 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_exp_10398
_database_code_depnum_ccdc_archive 'CCDC 2123098'
loop_
_audit_author_name
_audit_author_address
'HuangHaichao  '
;huaqiao university
China
;
_audit_update_record             
;
2021-11-19 deposited with the CCDC.	2021-11-26 downloaded from the CCDC.
;
_audit_creation_date             2021-11-19
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.06.29 svn.r12e2184c for OlexSys, GUI svn.r6374)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H10 F3 N'
_chemical_formula_sum            'C16 H10 F3 N'
_chemical_formula_weight         273.25
_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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   8.8679(15)
_cell_length_b                   14.9200(17)
_cell_length_c                   10.3319(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.788(16)
_cell_angle_gamma                90
_cell_volume                     1327.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    293.00(10)
_cell_measurement_theta_max      26.8000
_cell_measurement_theta_min      4.2990
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0646
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5807
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.278
_diffrn_reflns_theta_min         3.613
_diffrn_ambient_temperature      293.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  55.00   1.00    2.50    --   15.81 -99.00-120.00   69
  2  ω    -49.00  70.00   1.00    2.50    --   15.81   0.00 -90.00  119
  3  ω    -23.00   3.00   1.00    2.50    --  -16.43 -99.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0578058000
_diffrn_orient_matrix_UB_12      0.0203204000
_diffrn_orient_matrix_UB_13      0.0273203000
_diffrn_orient_matrix_UB_21      -0.0585909000
_diffrn_orient_matrix_UB_22      -0.0212135000
_diffrn_orient_matrix_UB_23      -0.0492126000
_diffrn_orient_matrix_UB_31      0.0018329000
_diffrn_orient_matrix_UB_32      -0.0373807000
_diffrn_orient_matrix_UB_33      0.0427774000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1435
_reflns_number_total             3050
_reflns_odcompleteness_completeness 99.12
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3050
_refine_ls_number_restraints     39
_refine_ls_R_factor_all          0.1358
_refine_ls_R_factor_gt           0.0636
_refine_ls_restrained_S_all      0.988
_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)+(0.0701P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1822
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1B-C10 \\sim F2-C10 \\sim F2B-C10 \\sim F3B-C10 \\sim F3-C10 \\sim F1-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1B) \\sim Ueq, Uanis(F2B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: F1(0.5) F3(0.5) F2(0.5) F1B(0.5) F2B(0.5) F3B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C6(H6), C12(H12), C8(H8), C7(H7), C13(H13), C16(H16),
 C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 0.5065(2) 0.66671(12) 0.43048(18) 0.0507(5) Uani 1 1 d . . . . .
C2 C 0.4462(3) 0.71311(14) 0.6355(2) 0.0485(6) Uani 1 1 d . . . . .
H2 H 0.465597 0.753732 0.705819 0.058 Uiso 1 1 calc R U . . .
C4 C 0.3110(3) 0.58769(13) 0.5179(2) 0.0428(5) Uani 1 1 d . . . . .
C5 C 0.3985(3) 0.60047(14) 0.4207(2) 0.0462(6) Uani 1 1 d . . . . .
C3 C 0.3383(3) 0.64690(13) 0.6292(2) 0.0432(6) Uani 1 1 d . . . . .
C1 C 0.5271(3) 0.71910(14) 0.5350(2) 0.0491(6) Uani 1 1 d . . . . .
C9 C 0.2012(3) 0.51780(14) 0.4968(2) 0.0572(7) Uani 1 1 d . . . . .
H9 H 0.142817 0.507814 0.559202 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3717(3) 0.54380(16) 0.3076(2) 0.0590(7) Uani 1 1 d . . . . .
H6 H 0.428034 0.552280 0.243313 0.071 Uiso 1 1 calc R U . . .
C11 C 0.2510(3) 0.64009(14) 0.7360(2) 0.0465(6) Uani 1 1 d . . . . .
C12 C 0.1687(3) 0.71247(15) 0.7657(2) 0.0572(7) Uani 1 1 d . . . . .
H12 H 0.165581 0.765321 0.717415 0.069 Uiso 1 1 calc R U . . .
C8 C 0.1790(3) 0.46454(16) 0.3869(3) 0.0664(8) Uani 1 1 d . . . . .
H8 H 0.105431 0.418970 0.374879 0.080 Uiso 1 1 calc R U . . .
C7 C 0.2653(3) 0.47764(17) 0.2923(3) 0.0659(8) Uani 1 1 d . . . . .
H7 H 0.249476 0.440520 0.217938 0.079 Uiso 1 1 calc R U . . .
C13 C 0.0908(3) 0.70737(18) 0.8663(3) 0.0685(8) Uani 1 1 d . . . . .
H13 H 0.035492 0.756593 0.885371 0.082 Uiso 1 1 calc R U . . .
C10 C 0.6489(4) 0.79097(19) 0.5436(3) 0.0696(8) Uani 1 1 d D . . . .
C16 C 0.2539(3) 0.56208(16) 0.8103(2) 0.0630(7) Uani 1 1 d . . . . .
H16 H 0.308460 0.512386 0.791741 0.076 Uiso 1 1 calc R U . . .
C14 C 0.0951(3) 0.6297(2) 0.9384(3) 0.0753(9) Uani 1 1 d . . . . .
H14 H 0.042224 0.626186 1.005903 0.090 Uiso 1 1 calc R U . . .
F1 F 0.7669(9) 0.7734(6) 0.6404(10) 0.129(3) Uani 0.5 1 d D U P A 1
F3 F 0.6970(13) 0.8019(7) 0.4376(6) 0.117(3) Uani 0.5 1 d D U P A 1
C15 C 0.1767(4) 0.55781(19) 0.9109(3) 0.0763(9) Uani 1 1 d . . . . .
H15 H 0.180379 0.505484 0.960450 0.092 Uiso 1 1 calc R U . . .
F2 F 0.5919(10) 0.8694(3) 0.5665(15) 0.131(3) Uani 0.5 1 d D . P A 1
F1B F 0.7045(13) 0.8235(7) 0.6615(5) 0.106(2) Uani 0.5 1 d D U P A 2
F2B F 0.6018(10) 0.8595(6) 0.4685(13) 0.141(3) Uani 0.5 1 d D U P A 2
F3B F 0.7728(11) 0.7615(5) 0.5067(16) 0.147(3) Uani 0.5 1 d D . P A 2


_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
N1 C5 1.363(3) . ?
N1 C1 1.310(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.366(3) . ?
C2 C1 1.399(3) . ?
C4 C5 1.420(3) . ?
C4 C3 1.425(3) . ?
C4 C9 1.407(3) . ?
C5 C6 1.416(3) . ?
C3 C11 1.495(3) . ?
C1 C10 1.510(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.362(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.349(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.391(3) . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C10 F1 1.290(5) . ?
C10 F3 1.277(5) . ?
C10 F2 1.318(5) . ?
C10 F1B 1.295(5) . ?
C10 F2B 1.291(5) . ?
C10 F3B 1.321(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.361(4) . ?
C15 H15 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 N1 C5 116.81(18) . . ?
C3 C2 H2 120.4 . . ?
C3 C2 C1 119.2(2) . . ?
C1 C2 H2 120.4 . . ?
C5 C4 C3 118.09(19) . . ?
C9 C4 C5 117.69(19) . . ?
C9 C4 C3 124.22(19) . . ?
N1 C5 C4 122.52(18) . . ?
N1 C5 C6 118.08(19) . . ?
C6 C5 C4 119.4(2) . . ?
C2 C3 C4 118.01(18) . . ?
C2 C3 C11 119.61(18) . . ?
C4 C3 C11 122.37(19) . . ?
N1 C1 C2 125.3(2) . . ?
N1 C1 C10 115.4(2) . . ?
C2 C1 C10 119.2(2) . . ?
C4 C9 H9 119.4 . . ?
C8 C9 C4 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C12 C11 C3 120.39(19) . . ?
C12 C11 C16 118.3(2) . . ?
C16 C11 C3 121.3(2) . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.7(2) . . ?
C13 C12 H12 119.6 . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C7 C8 H8 119.7 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13 120.0 . . ?
F1 C10 C1 109.8(3) . . ?
F1 C10 F2 108.4(5) . . ?
F3 C10 C1 114.9(3) . . ?
F3 C10 F1 108.4(5) . . ?
F3 C10 F2 105.1(5) . . ?
F2 C10 C1 110.0(3) . . ?
F1B C10 C1 115.4(3) . . ?
F1B C10 F3B 103.9(6) . . ?
F2B C10 C1 113.7(4) . . ?
F2B C10 F1B 105.4(5) . . ?
F2B C10 F3B 105.2(5) . . ?
F3B C10 C1 112.3(4) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.0 . . ?
C16 C15 H15 119.8 . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 119.8 . . ?

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
N1 C5 C6 C7 -179.5(2) . . . . ?
N1 C1 C10 F1 -110.7(8) . . . . ?
N1 C1 C10 F3 11.8(8) . . . . ?
N1 C1 C10 F2 130.1(7) . . . . ?
N1 C1 C10 F1B -159.0(7) . . . . ?
N1 C1 C10 F2B 79.0(9) . . . . ?
N1 C1 C10 F3B -40.3(9) . . . . ?
C2 C3 C11 C12 55.4(3) . . . . ?
C2 C3 C11 C16 -122.7(3) . . . . ?
C2 C1 C10 F1 69.4(8) . . . . ?
C2 C1 C10 F3 -168.1(8) . . . . ?
C2 C1 C10 F2 -49.8(8) . . . . ?
C2 C1 C10 F1B 21.1(8) . . . . ?
C2 C1 C10 F2B -100.9(9) . . . . ?
C2 C1 C10 F3B 139.8(8) . . . . ?
C4 C5 C6 C7 -0.6(4) . . . . ?
C4 C3 C11 C12 -123.1(2) . . . . ?
C4 C3 C11 C16 58.8(3) . . . . ?
C4 C9 C8 C7 0.3(4) . . . . ?
C5 N1 C1 C2 -0.8(3) . . . . ?
C5 N1 C1 C10 179.3(2) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C5 C4 C3 C11 179.12(19) . . . . ?
C5 C4 C9 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C3 C2 C1 N1 1.5(4) . . . . ?
C3 C2 C1 C10 -178.6(2) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C3 C4 C5 C6 -178.8(2) . . . . ?
C3 C4 C9 C8 178.8(2) . . . . ?
C3 C11 C12 C13 -178.4(2) . . . . ?
C3 C11 C16 C15 178.0(2) . . . . ?
C1 N1 C5 C4 0.1(3) . . . . ?
C1 N1 C5 C6 178.9(2) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C1 C2 C3 C11 -179.8(2) . . . . ?
C9 C4 C5 N1 179.3(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C9 C4 C3 C2 -178.6(2) . . . . ?
C9 C4 C3 C11 -0.1(3) . . . . ?
C9 C8 C7 C6 -0.5(4) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C11 C16 C15 C14 0.6(4) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C16 C11 C12 C13 -0.2(4) . . . . ?

_olex2_date_sample_data_collection 2021-11-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 5.074
_oxdiff_exptl_absorpt_empirical_full_min 0.408
