# 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_d8v21507_0m
_database_code_depnum_ccdc_archive 'CCDC 2100730'
loop_
_audit_author_name
_audit_author_address
yangxiu
;the university of Donghua
China
;
_audit_update_record             
;
2021-08-01 deposited with the CCDC.	2021-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H17 F3 N2 O'
_chemical_formula_weight         346.34

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                   11.9256(4)
_cell_length_b                   11.4661(4)
_cell_length_c                   12.6607(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.6160(10)
_cell_angle_gamma                90
_cell_volume                     1640.65(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    3873
_cell_measurement_theta_min      4.914
_cell_measurement_theta_max      54.826

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8037
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.353
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3205
_reflns_number_gt                2597
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0345P)²+0.5963P] 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     SHELXL
_refine_ls_extinction_coef       0.025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0399
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0881
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_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
F1 F 0.30824(11) 1.00437(10) -0.01604(8) 0.0628(3) Uani 1 1 d . . . . .
F2 F 0.33239(12) 1.05154(9) 0.15211(9) 0.0652(4) Uani 1 1 d . . . . .
F3 F 0.46846(10) 0.95946(11) 0.11099(10) 0.0669(4) Uani 1 1 d . . . . .
O1 O 0.68784(10) 0.70234(10) 0.30050(11) 0.0487(3) Uani 1 1 d . . . . .
N1 N 0.39710(11) 0.59365(11) 0.17615(10) 0.0315(3) Uani 1 1 d . . . . .
N2 N 0.63217(11) 0.53018(11) 0.20802(10) 0.0332(3) Uani 1 1 d . . . . .
C1 C 0.54140(14) 0.45629(13) 0.14795(12) 0.0315(3) Uani 1 1 d . . . . .
C2 C 0.56339(16) 0.35001(14) 0.10356(14) 0.0404(4) Uani 1 1 d . . . . .
H2 H 0.6415 0.3258 0.1139 0.048 Uiso 1 1 calc R U . . .
C3 C 0.46951(17) 0.28133(15) 0.04462(14) 0.0459(4) Uani 1 1 d . . . . .
H3 H 0.4846 0.2101 0.0149 0.055 Uiso 1 1 calc R U . . .
C4 C 0.35331(17) 0.31447(15) 0.02794(14) 0.0446(4) Uani 1 1 d . . . . .
H4 H 0.2904 0.2666 -0.0130 0.053 Uiso 1 1 calc R U . . .
C5 C 0.33122(14) 0.41816(14) 0.07212(13) 0.0372(4) Uani 1 1 d . . . . .
H5 H 0.2527 0.4410 0.0616 0.045 Uiso 1 1 calc R U . . .
C6 C 0.42435(13) 0.49004(13) 0.13260(12) 0.0308(3) Uani 1 1 d . . . . .
C7 C 0.48260(13) 0.66085(13) 0.23089(12) 0.0303(3) Uani 1 1 d . . . . .
C8 C 0.60951(13) 0.63466(13) 0.25011(13) 0.0331(3) Uani 1 1 d . . . . .
C9 C 0.75589(14) 0.49933(17) 0.22439(15) 0.0463(4) Uani 1 1 d . . . . .
H9A H 0.7744 0.4260 0.2645 0.069 Uiso 1 1 calc R U . . .
H9B H 0.8072 0.5601 0.2671 0.069 Uiso 1 1 calc R U . . .
H9C H 0.7679 0.4915 0.1525 0.069 Uiso 1 1 calc R U . . .
C10 C 0.45729(13) 0.77277(13) 0.28203(12) 0.0308(3) Uani 1 1 d . . . . .
H10 H 0.5112 0.8337 0.2708 0.037 Uiso 1 1 calc R U . . .
C11 C 0.48115(13) 0.75863(13) 0.40719(12) 0.0317(3) Uani 1 1 d . . . . .
C12 C 0.53725(16) 0.84707(14) 0.47893(14) 0.0429(4) Uani 1 1 d . . . . .
H12 H 0.5662 0.9122 0.4506 0.052 Uiso 1 1 calc R U . . .
C13 C 0.55150(18) 0.84139(16) 0.59151(15) 0.0507(5) Uani 1 1 d . . . . .
H13 H 0.5890 0.9028 0.6388 0.061 Uiso 1 1 calc R U . . .
C14 C 0.51106(16) 0.74627(17) 0.63458(14) 0.0489(5) Uani 1 1 d . . . . .
H14 H 0.5205 0.7424 0.7111 0.059 Uiso 1 1 calc R U . . .
C15 C 0.45660(17) 0.65651(17) 0.56460(15) 0.0497(5) Uani 1 1 d . . . . .
H15 H 0.4295 0.5908 0.5936 0.060 Uiso 1 1 calc R U . . .
C16 C 0.44150(15) 0.66277(15) 0.45120(14) 0.0422(4) Uani 1 1 d . . . . .
H16 H 0.4040 0.6012 0.4040 0.051 Uiso 1 1 calc R U . . .
C17 C 0.32945(14) 0.81492(14) 0.22744(12) 0.0344(4) Uani 1 1 d . . . . .
H17A H 0.2758 0.7518 0.2320 0.041 Uiso 1 1 calc R U . . .
H17B H 0.3152 0.8805 0.2711 0.041 Uiso 1 1 calc R U . . .
C18 C 0.29720(15) 0.85335(14) 0.10597(13) 0.0366(4) Uani 1 1 d . . . . .
H18A H 0.3218 0.7923 0.0639 0.044 Uiso 1 1 calc R U . . .
H18B H 0.2110 0.8604 0.0752 0.044 Uiso 1 1 calc R U . . .
C19 C 0.35100(15) 0.96531(14) 0.08862(13) 0.0400(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
F1 C19 1.3360(18) . ?
F2 C19 1.3368(19) . ?
F3 C19 1.339(2) . ?
O1 C8 1.2252(18) . ?
N1 C7 1.2894(19) . ?
N1 C6 1.3912(18) . ?
N2 C8 1.3726(19) . ?
N2 C1 1.394(2) . ?
N2 C9 1.4662(19) . ?
C1 C6 1.401(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.377(2) . ?
C2 H2 0.9400 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.399(2) . ?
C5 H5 0.9400 . ?
C7 C8 1.485(2) . ?
C7 C10 1.511(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.527(2) . ?
C10 C17 1.537(2) . ?
C10 H10 0.9900 . ?
C11 C16 1.382(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.382(2) . ?
C12 H12 0.9400 . ?
C13 C14 1.374(3) . ?
C13 H13 0.9400 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9400 . ?
C15 C16 1.391(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C18 1.526(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.482(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 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
C7 N1 C6 118.60(13) . . ?
C8 N2 C1 121.84(12) . . ?
C8 N2 C9 118.01(13) . . ?
C1 N2 C9 120.11(13) . . ?
N2 C1 C6 118.28(13) . . ?
N2 C1 C2 122.36(14) . . ?
C6 C1 C2 119.36(15) . . ?
C3 C2 C1 119.38(16) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.73(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 119.15(16) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 120.71(15) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C5 118.37(14) . . ?
N1 C6 C1 121.95(14) . . ?
C5 C6 C1 119.67(14) . . ?
N1 C7 C8 123.85(13) . . ?
N1 C7 C10 120.41(13) . . ?
C8 C7 C10 115.73(13) . . ?
O1 C8 N2 122.89(14) . . ?
O1 C8 C7 121.67(14) . . ?
N2 C8 C7 115.44(13) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 110.98(12) . . ?
C7 C10 C17 112.31(12) . . ?
C11 C10 C17 109.24(11) . . ?
C7 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C17 C10 H10 108.1 . . ?
C16 C11 C12 118.32(14) . . ?
C16 C11 C10 121.90(14) . . ?
C12 C11 C10 119.64(14) . . ?
C13 C12 C11 121.14(16) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.24(17) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 119.40(16) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.30(17) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C11 C16 C15 120.59(16) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C10 116.01(12) . . ?
C18 C17 H17A 108.3 . . ?
C10 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C10 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 114.68(13) . . ?
C19 C18 H18A 108.6 . . ?
C17 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.6 . . ?
F1 C19 F2 105.33(13) . . ?
F1 C19 F3 105.60(14) . . ?
F2 C19 F3 105.85(14) . . ?
F1 C19 C18 113.02(14) . . ?
F2 C19 C18 112.86(13) . . ?
F3 C19 C18 113.46(14) . . ?

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
C8 N2 C1 C6 -1.1(2) . . . . ?
C9 N2 C1 C6 -178.90(14) . . . . ?
C8 N2 C1 C2 179.31(14) . . . . ?
C9 N2 C1 C2 1.6(2) . . . . ?
N2 C1 C2 C3 -179.74(14) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 0.0(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C7 N1 C6 C5 -179.22(14) . . . . ?
C7 N1 C6 C1 0.9(2) . . . . ?
C4 C5 C6 N1 -179.57(14) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
N2 C1 C6 N1 -0.6(2) . . . . ?
C2 C1 C6 N1 179.00(13) . . . . ?
N2 C1 C6 C5 179.61(13) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C6 N1 C7 C8 0.3(2) . . . . ?
C6 N1 C7 C10 -178.51(12) . . . . ?
C1 N2 C8 O1 -177.95(14) . . . . ?
C9 N2 C8 O1 -0.1(2) . . . . ?
C1 N2 C8 C7 2.2(2) . . . . ?
C9 N2 C8 C7 -179.97(13) . . . . ?
N1 C7 C8 O1 178.31(15) . . . . ?
C10 C7 C8 O1 -2.8(2) . . . . ?
N1 C7 C8 N2 -1.9(2) . . . . ?
C10 C7 C8 N2 177.00(12) . . . . ?
N1 C7 C10 C11 101.94(16) . . . . ?
C8 C7 C10 C11 -76.98(15) . . . . ?
N1 C7 C10 C17 -20.67(19) . . . . ?
C8 C7 C10 C17 160.42(12) . . . . ?
C7 C10 C11 C16 -45.93(19) . . . . ?
C17 C10 C11 C16 78.43(18) . . . . ?
C7 C10 C11 C12 138.34(15) . . . . ?
C17 C10 C11 C12 -97.29(17) . . . . ?
C16 C11 C12 C13 -1.3(3) . . . . ?
C10 C11 C12 C13 174.60(15) . . . . ?
C11 C12 C13 C14 0.8(3) . . . . ?
C12 C13 C14 C15 0.2(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C12 C11 C16 C15 0.8(2) . . . . ?
C10 C11 C16 C15 -175.02(15) . . . . ?
C14 C15 C16 C11 0.2(3) . . . . ?
C7 C10 C17 C18 -66.43(17) . . . . ?
C11 C10 C17 C18 169.98(13) . . . . ?
C10 C17 C18 C19 -71.56(18) . . . . ?
C17 C18 C19 F1 -171.19(13) . . . . ?
C17 C18 C19 F2 -51.80(19) . . . . ?
C17 C18 C19 F3 68.61(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C18 H18A N1 0.98 2.68 3.225(2) 115.2 .
C10 H10 F3 0.99 2.40 3.0777(18) 124.9 .
C2 H2 O1 0.94 2.43 3.293(2) 152.3 2_645

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.033

_shelxl_version_number           2013-4

