# 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_exp_10507
_database_code_depnum_ccdc_archive 'CCDC 2246278'
loop_
_audit_author_name
_audit_author_address
'yongjian Jiao'
;yongjuan Jiao
China
;
_audit_update_record             
;
2023-03-04 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;
_audit_creation_date             2023-03-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        CCD
_chemical_formula_moiety         'C18 H14 F3 N O2'
_chemical_formula_sum            'C18 H14 F3 N O2'
_chemical_formula_weight         333.30
_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      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                   9.9693(8)
_cell_length_b                   11.1128(9)
_cell_length_c                   14.6773(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.872(7)
_cell_angle_gamma                90
_cell_volume                     1617.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2068
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0480
_cell_measurement_theta_min      3.9160
_shelx_estimated_absorpt_T_max   1.000
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87983
_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            ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7401
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.148
_diffrn_reflns_theta_min         3.631
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_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      2.00  81.00   1.00    5.00    --   15.65  57.00  90.00   79
  2  ω     35.00  60.00   1.00    5.00    --   15.65 178.00 -60.00   25
  3  ω     36.00  68.00   1.00    5.00    --   15.65 178.00-150.00   32
  4  ω    -53.00  24.00   1.00    5.00    --   15.65 -38.00 -30.00   77
;
_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      -0.0099683000
_diffrn_orient_matrix_UB_12      0.0270304000
_diffrn_orient_matrix_UB_13      0.0425226000
_diffrn_orient_matrix_UB_21      0.0694844000
_diffrn_orient_matrix_UB_22      -0.0075238000
_diffrn_orient_matrix_UB_23      0.0148049000
_diffrn_orient_matrix_UB_31      0.0136642000
_diffrn_orient_matrix_UB_32      0.0573903000
_diffrn_orient_matrix_UB_33      -0.0181572000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2390
_reflns_number_total             3682
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1179
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.032
_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)+(0.0817P)²+1.1684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1849
_refine_ls_wR_factor_ref         0.2117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00I),
 C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00B,H00C)
;
_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
O001 O 0.3761(2) 0.4062(2) 0.25370(14) 0.0654(6) Uani 1 1 d . . . . .
O002 O 0.5842(2) 0.4820(2) 0.26724(15) 0.0687(7) Uani 1 1 d . . . . .
N003 N 0.1967(2) 0.5596(2) 0.33626(14) 0.0448(6) Uani 1 1 d . . . . .
F004 F -0.0860(2) 0.4076(3) 0.32235(17) 0.1316(12) Uani 1 1 d . . . . .
C005 C 0.3179(3) 0.5948(2) 0.38742(17) 0.0410(6) Uani 1 1 d . . . . .
C006 C 0.1403(3) 0.4604(2) 0.34677(16) 0.0416(6) Uani 1 1 d . . . . .
C007 C 0.1773(3) 0.3661(2) 0.41658(17) 0.0411(6) Uani 1 1 d . . . . .
C008 C 0.3010(3) 0.6851(2) 0.45925(17) 0.0426(6) Uani 1 1 d . . . . .
C009 C 0.4377(3) 0.5593(3) 0.36354(18) 0.0478(7) Uani 1 1 d . . . . .
H009 H 0.5143 0.5915 0.3961 0.057 Uiso 1 1 calc R U . . .
F00A F 0.0319(3) 0.3512(3) 0.2255(2) 0.1565(16) Uani 1 1 d . . . . .
C00B C 0.4576(3) 0.4744(3) 0.29065(18) 0.0475(7) Uani 1 1 d . . . . .
F00C F -0.0217(3) 0.5273(3) 0.2303(2) 0.1587(16) Uani 1 1 d . . . . .
C00D C 0.1865(3) 0.3968(3) 0.50803(18) 0.0526(7) Uani 1 1 d . . . . .
H00D H 0.1712 0.4758 0.5250 0.063 Uiso 1 1 calc R U . . .
C00E C 0.4070(3) 0.7135(3) 0.5250(2) 0.0566(8) Uani 1 1 d . . . . .
H00E H 0.4904 0.6766 0.5230 0.068 Uiso 1 1 calc R U . . .
C00F C 0.1784(3) 0.7428(3) 0.4637(2) 0.0575(8) Uani 1 1 d . . . . .
H00F H 0.1064 0.7261 0.4201 0.069 Uiso 1 1 calc R U . . .
C00G C 0.2011(4) 0.2485(3) 0.3925(2) 0.0617(8) Uani 1 1 d . . . . .
H00G H 0.1953 0.2267 0.3310 0.074 Uiso 1 1 calc R U . . .
C00H C 0.0162(3) 0.4375(3) 0.2804(2) 0.0563(8) Uani 1 1 d . . . . .
C00I C 0.2182(3) 0.3107(4) 0.5744(2) 0.0672(10) Uani 1 1 d . . . . .
H00I H 0.2234 0.3318 0.6360 0.081 Uiso 1 1 calc R U . . .
C00J C 0.3894(4) 0.7957(3) 0.5931(2) 0.0699(10) Uani 1 1 d . . . . .
H00J H 0.4609 0.8137 0.6367 0.084 Uiso 1 1 calc R U . . .
C00K C 0.1626(4) 0.8249(3) 0.5325(3) 0.0710(10) Uani 1 1 d . . . . .
H00K H 0.0797 0.8625 0.5351 0.085 Uiso 1 1 calc R U . . .
C00L C 0.2672(4) 0.8512(3) 0.5968(2) 0.0711(10) Uani 1 1 d . . . . .
H00L H 0.2557 0.9065 0.6429 0.085 Uiso 1 1 calc R U . . .
C00M C 0.2421(4) 0.1951(4) 0.5504(3) 0.0722(10) Uani 1 1 d . . . . .
H00M H 0.2643 0.1375 0.5954 0.087 Uiso 1 1 calc R U . . .
C00N C 0.6163(4) 0.4012(4) 0.1955(3) 0.0806(11) Uani 1 1 d . . . . .
H00A H 0.5566 0.4162 0.1411 0.121 Uiso 1 1 calc R U . . .
H00B H 0.6058 0.3195 0.2148 0.121 Uiso 1 1 calc R U . . .
H00C H 0.7078 0.4141 0.1829 0.121 Uiso 1 1 calc R U . . .
C00O C 0.2333(4) 0.1634(3) 0.4593(3) 0.0788(11) Uani 1 1 d . . . . .
H00O H 0.2491 0.0843 0.4428 0.095 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
O001 C00B 1.199(3) . ?
O002 C00B 1.344(3) . ?
O002 C00N 1.445(4) . ?
N003 C005 1.411(3) . ?
N003 C006 1.254(3) . ?
F004 C00H 1.287(4) . ?
C005 C008 1.478(4) . ?
C005 C009 1.338(4) . ?
C006 C007 1.486(4) . ?
C006 C00H 1.516(4) . ?
C007 C00D 1.379(4) . ?
C007 C00G 1.380(4) . ?
C008 C00E 1.392(4) . ?
C008 C00F 1.388(4) . ?
C009 H009 0.9300 . ?
C009 C00B 1.456(4) . ?
F00A C00H 1.272(4) . ?
F00C C00H 1.273(4) . ?
C00D H00D 0.9300 . ?
C00D C00I 1.379(4) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.378(4) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.381(5) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.376(5) . ?
C00I H00I 0.9300 . ?
C00I C00M 1.359(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.371(5) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.365(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00O 1.376(5) . ?
C00N H00A 0.9600 . ?
C00N H00B 0.9600 . ?
C00N H00C 0.9600 . ?
C00O H00O 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
C00B O002 C00N 115.5(2) . . ?
C006 N003 C005 123.3(2) . . ?
N003 C005 C008 114.5(2) . . ?
C009 C005 N003 121.1(2) . . ?
C009 C005 C008 123.8(2) . . ?
N003 C006 C007 128.5(2) . . ?
N003 C006 C00H 114.6(2) . . ?
C007 C006 C00H 117.0(2) . . ?
C00D C007 C006 118.9(2) . . ?
C00D C007 C00G 119.2(3) . . ?
C00G C007 C006 121.9(2) . . ?
C00E C008 C005 121.0(3) . . ?
C00F C008 C005 120.8(3) . . ?
C00F C008 C00E 118.2(3) . . ?
C005 C009 H009 117.4 . . ?
C005 C009 C00B 125.2(3) . . ?
C00B C009 H009 117.4 . . ?
O001 C00B O002 122.3(3) . . ?
O001 C00B C009 127.2(3) . . ?
O002 C00B C009 110.5(2) . . ?
C007 C00D H00D 119.9 . . ?
C007 C00D C00I 120.2(3) . . ?
C00I C00D H00D 119.9 . . ?
C008 C00E H00E 119.7 . . ?
C00J C00E C008 120.6(3) . . ?
C00J C00E H00E 119.7 . . ?
C008 C00F H00F 119.8 . . ?
C00K C00F C008 120.4(3) . . ?
C00K C00F H00F 119.8 . . ?
C007 C00G H00G 120.0 . . ?
C00O C00G C007 120.1(3) . . ?
C00O C00G H00G 120.0 . . ?
F004 C00H C006 111.7(2) . . ?
F00A C00H F004 105.3(3) . . ?
F00A C00H C006 112.8(3) . . ?
F00A C00H F00C 105.9(3) . . ?
F00C C00H F004 106.0(3) . . ?
F00C C00H C006 114.4(3) . . ?
C00D C00I H00I 119.8 . . ?
C00M C00I C00D 120.4(3) . . ?
C00M C00I H00I 119.8 . . ?
C00E C00J H00J 119.8 . . ?
C00L C00J C00E 120.4(3) . . ?
C00L C00J H00J 119.8 . . ?
C00F C00K H00K 119.6 . . ?
C00L C00K C00F 120.7(3) . . ?
C00L C00K H00K 119.6 . . ?
C00J C00L H00L 120.2 . . ?
C00K C00L C00J 119.7(3) . . ?
C00K C00L H00L 120.2 . . ?
C00I C00M H00M 120.1 . . ?
C00I C00M C00O 119.9(3) . . ?
C00O C00M H00M 120.1 . . ?
O002 C00N H00A 109.5 . . ?
O002 C00N H00B 109.5 . . ?
O002 C00N H00C 109.5 . . ?
H00A C00N H00B 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00B C00N H00C 109.5 . . ?
C00G C00O C00M 120.2(3) . . ?
C00G C00O H00O 119.9 . . ?
C00M C00O H00O 119.9 . . ?

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
N003 C005 C008 C00E 169.0(2) . . . . ?
N003 C005 C008 C00F -10.0(4) . . . . ?
N003 C005 C009 C00B -6.1(4) . . . . ?
N003 C006 C007 C00D 55.9(4) . . . . ?
N003 C006 C007 C00G -125.0(3) . . . . ?
N003 C006 C00H F004 -127.9(3) . . . . ?
N003 C006 C00H F00A 113.7(4) . . . . ?
N003 C006 C00H F00C -7.5(4) . . . . ?
C005 N003 C006 C007 5.7(4) . . . . ?
C005 N003 C006 C00H -176.1(2) . . . . ?
C005 C008 C00E C00J -178.4(3) . . . . ?
C005 C008 C00F C00K 178.3(3) . . . . ?
C005 C009 C00B O001 -15.9(5) . . . . ?
C005 C009 C00B O002 163.3(3) . . . . ?
C006 N003 C005 C008 -105.0(3) . . . . ?
C006 N003 C005 C009 83.0(3) . . . . ?
C006 C007 C00D C00I 178.8(3) . . . . ?
C006 C007 C00G C00O -179.1(3) . . . . ?
C007 C006 C00H F004 50.5(4) . . . . ?
C007 C006 C00H F00A -67.9(4) . . . . ?
C007 C006 C00H F00C 170.9(3) . . . . ?
C007 C00D C00I C00M 0.6(5) . . . . ?
C007 C00G C00O C00M -0.1(6) . . . . ?
C008 C005 C009 C00B -177.3(2) . . . . ?
C008 C00E C00J C00L -0.2(5) . . . . ?
C008 C00F C00K C00L 0.4(5) . . . . ?
C009 C005 C008 C00E -19.2(4) . . . . ?
C009 C005 C008 C00F 161.7(3) . . . . ?
C00D C007 C00G C00O 0.1(5) . . . . ?
C00D C00I C00M C00O -0.6(5) . . . . ?
C00E C008 C00F C00K -0.8(4) . . . . ?
C00E C00J C00L C00K -0.1(6) . . . . ?
C00F C008 C00E C00J 0.7(4) . . . . ?
C00F C00K C00L C00J 0.0(6) . . . . ?
C00G C007 C00D C00I -0.4(4) . . . . ?
C00H C006 C007 C00D -122.2(3) . . . . ?
C00H C006 C007 C00G 56.9(4) . . . . ?
C00I C00M C00O C00G 0.3(6) . . . . ?
C00N O002 C00B O001 -0.9(4) . . . . ?
C00N O002 C00B C009 179.7(3) . . . . ?

_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 1.232
_oxdiff_exptl_absorpt_empirical_full_min 0.879
