# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_lmh01_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2fsdsf
_database_code_depnum_ccdc_archive 'CCDC 2257785'
loop_
_audit_author_name
_audit_author_address
'Frank Allen'
;Tianjin university
China
;
_audit_update_record             
;
2023-04-20 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 F3 N2'
_chemical_formula_sum            'C16 H11 F3 N2'
_chemical_formula_weight         288.27
_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                   5.6195(5)
_cell_length_b                   18.5139(15)
_cell_length_c                   12.9119(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.887(3)
_cell_angle_gamma                90
_cell_volume                     1323.39(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5199
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.348
_cell_measurement_theta_min      2.721
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1361 before and 0.0616 after correction.
The Ratio of minimum to maximum transmission is 0.8729.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23856
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.641
_diffrn_reflns_theta_min         2.200
_diffrn_ambient_temperature      296.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  Rigaku_AFC12K_724P_007HF_Mo
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2518
_reflns_number_total             3722
_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       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0398P)²+0.3662P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1091
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C00G(H00G)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00H(H00H),
 C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L)
;
_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
F001 F 0.33457(16) 0.54746(5) 0.92116(6) 0.0367(2) Uani 1 1 d . . . . .
F002 F 0.50620(18) 0.57968(6) 0.51604(7) 0.0453(3) Uani 1 1 d . . . . .
F003 F 0.2592(2) 0.66669(5) 0.53652(8) 0.0509(3) Uani 1 1 d . . . . .
N004 N 0.1296(2) 0.50340(6) 0.76260(9) 0.0263(3) Uani 1 1 d . . . . .
N005 N 0.1153(2) 0.51499(7) 0.65754(9) 0.0287(3) Uani 1 1 d . . . . .
C006 C 0.3910(2) 0.59279(8) 0.75050(11) 0.0259(3) Uani 1 1 d . . . . .
C007 C 0.2915(2) 0.54934(8) 0.81688(11) 0.0259(3) Uani 1 1 d . . . . .
C008 C 0.5695(2) 0.65111(8) 0.77914(11) 0.0262(3) Uani 1 1 d . . . . .
C009 C 0.2718(3) 0.56814(8) 0.65099(11) 0.0275(3) Uani 1 1 d . . . . .
C00A C -0.0255(3) 0.45111(8) 0.79873(11) 0.0261(3) Uani 1 1 d . . . . .
C00B C 0.5538(3) 0.69638(8) 0.86400(12) 0.0317(3) Uani 1 1 d . . . . .
H00B H 0.431734 0.689348 0.903340 0.038 Uiso 1 1 calc R U . . .
C00C C -0.2518(3) 0.44018(8) 0.73824(12) 0.0289(3) Uani 1 1 d . . . . .
H00C H -0.301534 0.467440 0.677909 0.035 Uiso 1 1 calc R U . . .
C00D C -0.4024(3) 0.38819(8) 0.76894(13) 0.0349(4) Uani 1 1 d . . . . .
H00D H -0.553530 0.379911 0.728532 0.042 Uiso 1 1 calc R U . . .
C00E C 0.0509(3) 0.41186(8) 0.88967(12) 0.0322(3) Uani 1 1 d . . . . .
H00E H 0.202463 0.419753 0.929892 0.039 Uiso 1 1 calc R U . . .
C00F C 0.7552(3) 0.66252(8) 0.72177(13) 0.0317(3) Uani 1 1 d . . . . .
H00F H 0.769630 0.632388 0.665554 0.038 Uiso 1 1 calc R U . . .
C00G C 0.2851(3) 0.59332(9) 0.54303(12) 0.0352(4) Uani 1 1 d . . . . .
H00G H 0.158136 0.570040 0.492537 0.042 Uiso 1 1 calc R U . . .
C00H C 0.9182(3) 0.71847(9) 0.74805(13) 0.0358(4) Uani 1 1 d . . . . .
H00H H 1.040302 0.725990 0.708909 0.043 Uiso 1 1 calc R U . . .
C00I C 0.9003(3) 0.76310(9) 0.83197(13) 0.0373(4) Uani 1 1 d . . . . .
H00I H 1.009941 0.800622 0.849321 0.045 Uiso 1 1 calc R U . . .
C00J C 0.7191(3) 0.75186(9) 0.89006(13) 0.0375(4) Uani 1 1 d . . . . .
H00J H 0.707834 0.781650 0.947004 0.045 Uiso 1 1 calc R U . . .
C00K C -0.1040(3) 0.36053(9) 0.91935(14) 0.0378(4) Uani 1 1 d . . . . .
H00K H -0.056167 0.333810 0.980360 0.045 Uiso 1 1 calc R U . . .
C00L C -0.3291(3) 0.34865(9) 0.85914(14) 0.0384(4) Uani 1 1 d . . . . .
H00L H -0.431126 0.313889 0.879632 0.046 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
F001 C007 1.3269(16) . ?
F002 C00G 1.3701(19) . ?
F003 C00G 1.3672(18) . ?
N004 N005 1.3621(16) . ?
N004 C007 1.3504(18) . ?
N004 C00A 1.4331(18) . ?
N005 C009 1.3318(19) . ?
C006 C007 1.363(2) . ?
C006 C008 1.477(2) . ?
C006 C009 1.419(2) . ?
C008 C00B 1.394(2) . ?
C008 C00F 1.395(2) . ?
C009 C00G 1.484(2) . ?
C00A C00C 1.388(2) . ?
C00A C00E 1.385(2) . ?
C00B H00B 0.9300 . ?
C00B C00J 1.387(2) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.384(2) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.377(2) . ?
C00E H00E 0.9300 . ?
C00E C00K 1.386(2) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.386(2) . ?
C00G H00G 0.9800 . ?
C00H H00H 0.9300 . ?
C00H C00I 1.380(2) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.380(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00L 1.384(2) . ?
C00L H00L 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
N005 N004 C00A 119.70(12) . . ?
C007 N004 N005 109.68(11) . . ?
C007 N004 C00A 130.52(12) . . ?
C009 N005 N004 104.65(11) . . ?
C007 C006 C008 127.46(13) . . ?
C007 C006 C009 101.45(12) . . ?
C009 C006 C008 131.06(13) . . ?
F001 C007 N004 119.95(13) . . ?
F001 C007 C006 129.08(13) . . ?
N004 C007 C006 110.97(13) . . ?
C00B C008 C006 120.27(13) . . ?
C00B C008 C00F 118.71(14) . . ?
C00F C008 C006 121.02(13) . . ?
N005 C009 C006 113.24(13) . . ?
N005 C009 C00G 115.61(13) . . ?
C006 C009 C00G 131.11(14) . . ?
C00C C00A N004 117.71(13) . . ?
C00E C00A N004 120.88(13) . . ?
C00E C00A C00C 121.39(14) . . ?
C008 C00B H00B 119.8 . . ?
C00J C00B C008 120.35(15) . . ?
C00J C00B H00B 119.8 . . ?
C00A C00C H00C 120.4 . . ?
C00D C00C C00A 119.11(14) . . ?
C00D C00C H00C 120.4 . . ?
C00C C00D H00D 119.9 . . ?
C00L C00D C00C 120.20(15) . . ?
C00L C00D H00D 119.9 . . ?
C00A C00E H00E 120.8 . . ?
C00A C00E C00K 118.45(15) . . ?
C00K C00E H00E 120.8 . . ?
C008 C00F H00F 119.8 . . ?
C00H C00F C008 120.40(15) . . ?
C00H C00F H00F 119.8 . . ?
F002 C00G C009 112.06(13) . . ?
F002 C00G H00G 109.8 . . ?
F003 C00G F002 105.01(13) . . ?
F003 C00G C009 110.35(13) . . ?
F003 C00G H00G 109.8 . . ?
C009 C00G H00G 109.8 . . ?
C00F C00H H00H 119.8 . . ?
C00I C00H C00F 120.38(15) . . ?
C00I C00H H00H 119.8 . . ?
C00H C00I H00I 120.1 . . ?
C00H C00I C00J 119.76(15) . . ?
C00J C00I H00I 120.1 . . ?
C00B C00J H00J 119.8 . . ?
C00I C00J C00B 120.39(16) . . ?
C00I C00J H00J 119.8 . . ?
C00E C00K H00K 119.7 . . ?
C00L C00K C00E 120.69(15) . . ?
C00L C00K H00K 119.7 . . ?
C00D C00L C00K 120.15(15) . . ?
C00D C00L H00L 119.9 . . ?
C00K C00L H00L 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
N004 N005 C009 C006 -0.21(16) . . . . ?
N004 N005 C009 C00G -177.92(12) . . . . ?
N004 C00A C00C C00D 177.65(13) . . . . ?
N004 C00A C00E C00K -178.19(13) . . . . ?
N005 N004 C007 F001 -179.96(12) . . . . ?
N005 N004 C007 C006 -0.19(16) . . . . ?
N005 N004 C00A C00C -30.99(18) . . . . ?
N005 N004 C00A C00E 147.62(14) . . . . ?
N005 C009 C00G F002 -115.13(15) . . . . ?
N005 C009 C00G F003 128.23(14) . . . . ?
C006 C008 C00B C00J -179.04(13) . . . . ?
C006 C008 C00F C00H 178.53(14) . . . . ?
C006 C009 C00G F002 67.7(2) . . . . ?
C006 C009 C00G F003 -49.0(2) . . . . ?
C007 N004 N005 C009 0.24(15) . . . . ?
C007 N004 C00A C00C 145.14(15) . . . . ?
C007 N004 C00A C00E -36.3(2) . . . . ?
C007 C006 C008 C00B -38.8(2) . . . . ?
C007 C006 C008 C00F 141.76(16) . . . . ?
C007 C006 C009 N005 0.10(16) . . . . ?
C007 C006 C009 C00G 177.35(15) . . . . ?
C008 C006 C007 F001 -2.0(2) . . . . ?
C008 C006 C007 N004 178.23(13) . . . . ?
C008 C006 C009 N005 -177.98(14) . . . . ?
C008 C006 C009 C00G -0.7(3) . . . . ?
C008 C00B C00J C00I 0.3(2) . . . . ?
C008 C00F C00H C00I 0.7(2) . . . . ?
C009 C006 C007 F001 179.80(14) . . . . ?
C009 C006 C007 N004 0.06(15) . . . . ?
C009 C006 C008 C00B 138.80(16) . . . . ?
C009 C006 C008 C00F -40.6(2) . . . . ?
C00A N004 N005 C009 177.11(12) . . . . ?
C00A N004 C007 F001 3.6(2) . . . . ?
C00A N004 C007 C006 -176.62(13) . . . . ?
C00A C00C C00D C00L 0.9(2) . . . . ?
C00A C00E C00K C00L 0.3(2) . . . . ?
C00B C008 C00F C00H -0.9(2) . . . . ?
C00C C00A C00E C00K 0.4(2) . . . . ?
C00C C00D C00L C00K -0.3(2) . . . . ?
C00E C00A C00C C00D -0.9(2) . . . . ?
C00E C00K C00L C00D -0.3(2) . . . . ?
C00F C008 C00B C00J 0.4(2) . . . . ?
C00F C00H C00I C00J 0.1(2) . . . . ?
C00H C00I C00J C00B -0.6(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
