# 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_mo_210531_ysl0528_1_0m_tw
_database_code_depnum_ccdc_archive 'CCDC 2087515'
loop_
_audit_author_name
_audit_author_address
'Zhengkai Chen'
;Zhejiang Sci Tech University
China
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2021-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H14 F3 N3'
_chemical_formula_sum            'C13 H14 F3 N3'
_chemical_formula_weight         269.27
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1130(7)
_cell_length_b                   9.2581(9)
_cell_length_c                   11.9702(14)
_cell_angle_alpha                85.938(4)
_cell_angle_beta                 75.268(4)
_cell_angle_gamma                81.041(4)
_cell_volume                     646.84(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5261
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.18
_cell_measurement_theta_min      2.79
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.960
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1309 before and 0.0661 after correction.
The Ratio of minimum to maximum transmission is 0.8995.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2833
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.259
_diffrn_reflns_theta_min         2.228
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2320
_reflns_number_total             2833
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0715
_refine_ls_restrained_S_all      1.076
_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)+(0.1243P)²+0.7255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2301
_refine_ls_wR_factor_ref         0.2413
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.732(6)
 0.268(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9)
3.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_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
F1 F 0.1417(4) 0.3079(3) 0.9217(3) 0.0651(8) Uani 1 1 d . . . . .
F2 F 0.3592(4) 0.4688(2) 0.9068(2) 0.0542(7) Uani 1 1 d . . . . .
F3 F 0.1762(5) 0.4054(3) 1.0731(2) 0.0767(10) Uani 1 1 d . . . . .
N1 N 0.5184(5) 0.1848(3) 1.0800(2) 0.0297(6) Uani 1 1 d . . . . .
N2 N 0.7142(5) 0.0837(3) 1.0534(2) 0.0310(6) Uani 1 1 d . . . . .
N3 N 0.6438(4) 0.1795(3) 0.89014(19) 0.0230(5) Uani 1 1 d . . . . .
C1 C 0.2874(6) 0.3553(4) 0.9713(3) 0.0359(7) Uani 1 1 d . . . . .
C2 C 0.4806(5) 0.2396(3) 0.9815(2) 0.0257(6) Uani 1 1 d . . . . .
C3 C 0.7847(5) 0.0833(3) 0.9401(3) 0.0281(6) Uani 1 1 d . . . . .
H3 H 0.917065 0.023480 0.898688 0.034 Uiso 1 1 calc R . . . .
C4 C 0.6647(5) 0.2036(3) 0.7675(2) 0.0225(6) Uani 1 1 d . . . . .
C5 C 0.5173(6) 0.1484(4) 0.7167(3) 0.0366(8) Uani 1 1 d . . . . .
H5 H 0.402704 0.095124 0.761721 0.044 Uiso 1 1 calc R . . . .
C6 C 0.5394(6) 0.1719(4) 0.5985(3) 0.0358(8) Uani 1 1 d . . . . .
H6 H 0.436713 0.134919 0.563908 0.043 Uiso 1 1 calc R . . . .
C7 C 0.7065(5) 0.2477(3) 0.5292(2) 0.0220(6) Uani 1 1 d . . . . .
C8 C 0.8530(6) 0.2989(4) 0.5840(3) 0.0347(7) Uani 1 1 d . . . . .
H8 H 0.970861 0.349745 0.539079 0.042 Uiso 1 1 calc R . . . .
C9 C 0.8335(6) 0.2784(4) 0.7019(3) 0.0348(7) Uani 1 1 d . . . . .
H9 H 0.935469 0.315485 0.736961 0.042 Uiso 1 1 calc R . . . .
C10 C 0.7314(5) 0.2690(3) 0.3984(2) 0.0259(6) Uani 1 1 d . . . . .
C11 C 0.8947(7) 0.1390(4) 0.3383(3) 0.0419(8) Uani 1 1 d . . . . .
H11A H 1.043650 0.134545 0.355991 0.063 Uiso 1 1 calc GR . . . .
H11B H 0.913178 0.150987 0.254587 0.063 Uiso 1 1 calc GR . . . .
H11C H 0.831756 0.048216 0.365976 0.063 Uiso 1 1 calc GR . . . .
C12 C 0.5005(6) 0.2771(5) 0.3682(3) 0.0422(8) Uani 1 1 d . . . . .
H12A H 0.439151 0.184937 0.392087 0.063 Uiso 1 1 calc GR . . . .
H12B H 0.521081 0.293484 0.284637 0.063 Uiso 1 1 calc GR . . . .
H12C H 0.393539 0.357961 0.408691 0.063 Uiso 1 1 calc GR . . . .
C13 C 0.8298(7) 0.4104(4) 0.3520(3) 0.0387(8) Uani 1 1 d . . . . .
H13A H 0.731265 0.493852 0.393047 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.837173 0.423341 0.269178 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.983706 0.404128 0.363996 0.058 Uiso 1 1 calc GR . . . .


_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 1.328(4) . ?
F2 C1 1.323(4) . ?
F3 C1 1.313(4) . ?
N1 N2 1.381(4) . ?
N1 C2 1.311(4) . ?
N2 C3 1.314(4) . ?
N3 C2 1.363(4) . ?
N3 C3 1.357(4) . ?
N3 C4 1.445(3) . ?
C1 C2 1.490(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 C9 1.376(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.390(4) . ?
C7 C8 1.390(4) . ?
C7 C10 1.536(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.532(4) . ?
C10 C12 1.534(4) . ?
C10 C13 1.534(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C2 N1 N2 106.7(2) . . ?
C3 N2 N1 107.0(2) . . ?
C2 N3 C4 129.9(2) . . ?
C3 N3 C2 103.9(2) . . ?
C3 N3 C4 126.1(2) . . ?
F1 C1 C2 112.3(3) . . ?
F2 C1 F1 105.9(3) . . ?
F2 C1 C2 111.8(3) . . ?
F3 C1 F1 109.1(3) . . ?
F3 C1 F2 106.6(3) . . ?
F3 C1 C2 110.8(3) . . ?
N1 C2 N3 111.3(2) . . ?
N1 C2 C1 124.1(3) . . ?
N3 C2 C1 124.6(2) . . ?
N2 C3 N3 111.1(3) . . ?
N2 C3 H3 124.4 . . ?
N3 C3 H3 124.4 . . ?
C5 C4 N3 119.5(2) . . ?
C9 C4 N3 120.0(2) . . ?
C9 C4 C5 120.6(3) . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(3) . . ?
C6 C5 H5 120.5 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.4(3) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 C8 116.5(3) . . ?
C6 C7 C10 121.4(2) . . ?
C8 C7 C10 122.0(3) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 H8 118.8 . . ?
C4 C9 C8 119.2(3) . . ?
C4 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C11 C10 C7 108.3(2) . . ?
C11 C10 C12 109.1(3) . . ?
C11 C10 C13 108.8(3) . . ?
C12 C10 C7 111.4(2) . . ?
C12 C10 C13 107.9(3) . . ?
C13 C10 C7 111.3(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
F1 C1 C2 N1 -115.5(4) . . . . ?
F1 C1 C2 N3 66.1(4) . . . . ?
F2 C1 C2 N1 125.6(3) . . . . ?
F2 C1 C2 N3 -52.8(4) . . . . ?
F3 C1 C2 N1 6.8(5) . . . . ?
F3 C1 C2 N3 -171.6(3) . . . . ?
N1 N2 C3 N3 -0.2(4) . . . . ?
N2 N1 C2 N3 -0.2(3) . . . . ?
N2 N1 C2 C1 -178.8(3) . . . . ?
N3 C4 C5 C6 -179.8(3) . . . . ?
N3 C4 C9 C8 179.1(3) . . . . ?
C2 N1 N2 C3 0.2(3) . . . . ?
C2 N3 C3 N2 0.1(3) . . . . ?
C2 N3 C4 C5 -72.2(4) . . . . ?
C2 N3 C4 C9 109.2(4) . . . . ?
C3 N3 C2 N1 0.1(3) . . . . ?
C3 N3 C2 C1 178.6(3) . . . . ?
C3 N3 C4 C5 104.9(4) . . . . ?
C3 N3 C4 C9 -73.7(4) . . . . ?
C4 N3 C2 N1 177.6(3) . . . . ?
C4 N3 C2 C1 -3.8(5) . . . . ?
C4 N3 C3 N2 -177.6(3) . . . . ?
C4 C5 C6 C7 0.8(6) . . . . ?
C5 C4 C9 C8 0.6(5) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C5 C6 C7 C10 178.5(3) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
C6 C7 C10 C11 -89.2(4) . . . . ?
C6 C7 C10 C12 30.8(4) . . . . ?
C6 C7 C10 C13 151.2(3) . . . . ?
C7 C8 C9 C4 0.6(5) . . . . ?
C8 C7 C10 C11 88.8(4) . . . . ?
C8 C7 C10 C12 -151.2(3) . . . . ?
C8 C7 C10 C13 -30.7(4) . . . . ?
C9 C4 C5 C6 -1.2(5) . . . . ?
C10 C7 C8 C9 -179.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.732(6)
2 0.268(6)

