# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 1939452'
loop_
_audit_author_name
_audit_author_address
'Yunhe Lv'
;Anyang Normal University
China
;
_audit_update_record             
;
2019-07-09 deposited with the CCDC.	2020-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 F2 N O'
_chemical_formula_weight         387.41

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'
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'
F F 0.0171 0.0103 '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/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.515(3)
_cell_length_b                   8.4989(17)
_cell_length_c                   19.132(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.95(3)
_cell_angle_gamma                90
_cell_volume                     2024.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1753
_cell_measurement_theta_min      5.7070
_cell_measurement_theta_max      68.7970

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            10598
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.636
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        24.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3535
_reflns_number_gt                1570
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.1055P)²+1.0098P] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3535
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1782
_refine_ls_R_factor_gt           0.0997
_refine_ls_wR_factor_ref         0.3009
_refine_ls_wR_factor_gt          0.2524
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_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
C1 C 0.1125(5) -0.1261(9) 0.1848(4) 0.1007(19) Uani 1 1 d . . . . .
C2 C 0.1298(5) 0.0172(9) 0.2153(3) 0.1033(19) Uani 1 1 d . . . . .
H2A H 0.084635 0.055285 0.247100 0.124 Uiso 1 1 calc R U . . .
C3 C 0.2155(5) 0.1042(7) 0.1981(3) 0.0929(17) Uani 1 1 d . . . . .
H3A H 0.228784 0.202400 0.218712 0.111 Uiso 1 1 calc R U . . .
C4 C 0.2823(4) 0.0484(6) 0.1508(3) 0.0784(14) Uani 1 1 d . . . . .
C5 C 0.2621(5) -0.0984(7) 0.1214(3) 0.0937(17) Uani 1 1 d . . . . .
H5A H 0.306451 -0.138829 0.089650 0.112 Uiso 1 1 calc R U . . .
C6 C 0.1756(5) -0.1848(7) 0.1394(4) 0.1038(19) Uani 1 1 d . . . . .
H6A H 0.161621 -0.283774 0.119914 0.125 Uiso 1 1 calc R U . . .
C7 C 0.3743(5) 0.1385(7) 0.1351(3) 0.0813(15) Uani 1 1 d . . . . .
C8 C 0.4509(4) 0.2141(7) 0.1234(3) 0.0778(14) Uani 1 1 d . . . . .
C9 C 0.5429(4) 0.3123(6) 0.1186(3) 0.0725(13) Uani 1 1 d . . . . .
C10 C 0.5897(4) 0.3195(6) 0.0584(3) 0.0834(15) Uani 1 1 d . . . . .
H10A H 0.557463 0.259037 0.021561 0.100 Uiso 1 1 calc R U . . .
C11 C 0.6837(5) 0.4086(6) 0.0431(3) 0.0799(14) Uani 1 1 d . . . . .
C12 C 0.7717(5) 0.4349(7) 0.0909(3) 0.0926(17) Uani 1 1 d . . . . .
H12A H 0.771658 0.394798 0.136111 0.111 Uiso 1 1 calc R U . . .
C13 C 0.8600(5) 0.5183(8) 0.0743(4) 0.108(2) Uani 1 1 d . . . . .
H13A H 0.919295 0.532814 0.107207 0.129 Uiso 1 1 calc R U . . .
C14 C 0.8579(7) 0.5794(8) 0.0076(5) 0.111(2) Uani 1 1 d . . . . .
C15 C 0.7740(7) 0.5540(8) -0.0419(4) 0.112(2) Uani 1 1 d . . . . .
H15A H 0.775426 0.593658 -0.087150 0.135 Uiso 1 1 calc R U . . .
C16 C 0.6870(5) 0.4690(7) -0.0247(3) 0.0989(19) Uani 1 1 d . . . . .
H16A H 0.629416 0.451499 -0.058640 0.119 Uiso 1 1 calc R U . . .
C17 C 0.5781(4) 0.4060(6) 0.1847(2) 0.0746(14) Uani 1 1 d . . . . .
H17A H 0.618524 0.337962 0.218535 0.090 Uiso 1 1 calc R U . . .
H17B H 0.625118 0.490693 0.173170 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4848(4) 0.4736(6) 0.2172(3) 0.0733(14) Uani 1 1 d . . . . .
C19 C 0.3670(4) 0.4300(6) 0.3115(2) 0.0702(13) Uani 1 1 d . . . . .
C20 C 0.2799(4) 0.5164(6) 0.2873(3) 0.0790(14) Uani 1 1 d . . . . .
H20A H 0.275011 0.556834 0.241879 0.095 Uiso 1 1 calc R U . . .
C21 C 0.1981(4) 0.5454(7) 0.3290(3) 0.0909(16) Uani 1 1 d . . . . .
H21A H 0.138541 0.603236 0.310710 0.109 Uiso 1 1 calc R U . . .
C22 C 0.2029(5) 0.4901(7) 0.3975(3) 0.0873(16) Uani 1 1 d . . . . .
C23 C 0.2920(5) 0.4036(7) 0.4211(3) 0.0948(18) Uani 1 1 d . . . . .
H23A H 0.297888 0.365372 0.466905 0.114 Uiso 1 1 calc R U . . .
C24 C 0.3734(4) 0.3709(6) 0.3796(3) 0.0856(15) Uani 1 1 d . . . . .
H24A H 0.431939 0.310035 0.397104 0.103 Uiso 1 1 calc R U . . .
C25 C 0.1150(5) 0.5277(8) 0.4430(3) 0.119(2) Uani 1 1 d . . . . .
H25A H 0.060395 0.588968 0.416581 0.179 Uiso 1 1 calc R U . . .
H25B H 0.084142 0.431578 0.458028 0.179 Uiso 1 1 calc R U . . .
H25C H 0.144319 0.586394 0.483353 0.179 Uiso 1 1 calc R U . . .
N1 N 0.4528(3) 0.3934(5) 0.2718(2) 0.0739(12) Uani 1 1 d . . . . .
H1A H 0.488735 0.309869 0.283973 0.089 Uiso 1 1 calc R U . . .
O1 O 0.4400(3) 0.5943(4) 0.19318(17) 0.0835(11) Uani 1 1 d . . . . .
F1 F 0.0275(3) -0.2116(5) 0.2021(2) 0.1412(16) Uani 1 1 d . . . . .
F2 F 0.9439(3) 0.6622(5) -0.0094(3) 0.1613(19) 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
C1 C6 1.330(8) . ?
C1 C2 1.359(9) . ?
C1 F1 1.357(6) . ?
C2 C3 1.371(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.379(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(7) . ?
C4 C7 1.439(7) . ?
C5 C6 1.381(7) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.195(7) . ?
C8 C9 1.433(7) . ?
C9 C10 1.346(6) . ?
C9 C17 1.521(6) . ?
C10 C11 1.454(7) . ?
C10 H10A 0.9300 . ?
C11 C12 1.376(7) . ?
C11 C16 1.400(7) . ?
C12 C13 1.377(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.376(9) . ?
C13 H13A 0.9300 . ?
C14 F2 1.354(7) . ?
C14 C15 1.356(9) . ?
C15 C16 1.376(8) . ?
C15 H15A 0.9300 . ?
C16 H16A 0.9300 . ?
C17 C18 1.494(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O1 1.235(6) . ?
C18 N1 1.342(6) . ?
C19 C20 1.356(6) . ?
C19 C24 1.391(7) . ?
C19 N1 1.413(5) . ?
C20 C21 1.384(6) . ?
C20 H20A 0.9300 . ?
C21 C22 1.388(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.373(7) . ?
C22 C25 1.506(7) . ?
C23 C24 1.383(7) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
N1 H1A 0.8600 . ?

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
C6 C1 C2 122.5(6) . . ?
C6 C1 F1 119.5(7) . . ?
C2 C1 F1 118.0(7) . . ?
C1 C2 C3 118.3(6) . . ?
C1 C2 H2A 120.8 . . ?
C3 C2 H2A 120.8 . . ?
C2 C3 C4 121.0(6) . . ?
C2 C3 H3A 119.5 . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 C5 118.7(5) . . ?
C3 C4 C7 120.4(5) . . ?
C5 C4 C7 120.8(5) . . ?
C6 C5 C4 119.6(5) . . ?
C6 C5 H5A 120.2 . . ?
C4 C5 H5A 120.2 . . ?
C1 C6 C5 119.9(6) . . ?
C1 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C4 178.8(6) . . ?
C7 C8 C9 172.4(6) . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 C17 125.0(5) . . ?
C8 C9 C17 114.6(4) . . ?
C9 C10 C11 129.0(5) . . ?
C9 C10 H10A 115.5 . . ?
C11 C10 H10A 115.5 . . ?
C12 C11 C16 117.3(6) . . ?
C12 C11 C10 124.0(5) . . ?
C16 C11 C10 118.7(6) . . ?
C13 C12 C11 122.5(6) . . ?
C13 C12 H12A 118.8 . . ?
C11 C12 H12A 118.8 . . ?
C14 C13 C12 118.0(7) . . ?
C14 C13 H13A 121.0 . . ?
C12 C13 H13A 121.0 . . ?
F2 C14 C15 119.5(7) . . ?
F2 C14 C13 118.6(8) . . ?
C15 C14 C13 121.8(7) . . ?
C14 C15 C16 119.4(6) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C15 C16 C11 121.0(7) . . ?
C15 C16 H16A 119.5 . . ?
C11 C16 H16A 119.5 . . ?
C18 C17 C9 112.1(4) . . ?
C18 C17 H17A 109.2 . . ?
C9 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C9 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
O1 C18 N1 123.5(5) . . ?
O1 C18 C17 120.6(4) . . ?
N1 C18 C17 115.9(5) . . ?
C20 C19 C24 118.8(5) . . ?
C20 C19 N1 124.3(4) . . ?
C24 C19 N1 116.8(5) . . ?
C19 C20 C21 121.1(5) . . ?
C19 C20 H20A 119.5 . . ?
C21 C20 H20A 119.5 . . ?
C20 C21 C22 121.5(6) . . ?
C20 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
C23 C22 C21 116.5(5) . . ?
C23 C22 C25 122.7(6) . . ?
C21 C22 C25 120.7(6) . . ?
C22 C23 C24 122.7(5) . . ?
C22 C23 H23A 118.7 . . ?
C24 C23 H23A 118.7 . . ?
C23 C24 C19 119.4(5) . . ?
C23 C24 H24A 120.3 . . ?
C19 C24 H24A 120.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C18 N1 C19 127.7(4) . . ?
C18 N1 H1A 116.2 . . ?
C19 N1 H1A 116.2 . . ?

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
C6 C1 C2 C3 0.4(10) . . . . ?
F1 C1 C2 C3 180.0(5) . . . . ?
C1 C2 C3 C4 0.3(9) . . . . ?
C2 C3 C4 C5 -0.8(9) . . . . ?
C2 C3 C4 C7 -177.7(5) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C7 C4 C5 C6 177.5(5) . . . . ?
C2 C1 C6 C5 -0.6(10) . . . . ?
F1 C1 C6 C5 179.8(5) . . . . ?
C4 C5 C6 C1 0.1(9) . . . . ?
C8 C9 C10 C11 -178.9(5) . . . . ?
C17 C9 C10 C11 2.8(9) . . . . ?
C9 C10 C11 C12 35.7(9) . . . . ?
C9 C10 C11 C16 -145.8(6) . . . . ?
C16 C11 C12 C13 0.7(8) . . . . ?
C10 C11 C12 C13 179.2(5) . . . . ?
C11 C12 C13 C14 1.3(9) . . . . ?
C12 C13 C14 F2 179.7(5) . . . . ?
C12 C13 C14 C15 -2.7(10) . . . . ?
F2 C14 C15 C16 179.6(5) . . . . ?
C13 C14 C15 C16 2.1(10) . . . . ?
C14 C15 C16 C11 0.0(9) . . . . ?
C12 C11 C16 C15 -1.4(8) . . . . ?
C10 C11 C16 C15 -179.9(5) . . . . ?
C10 C9 C17 C18 136.5(5) . . . . ?
C8 C9 C17 C18 -41.8(6) . . . . ?
C9 C17 C18 O1 -79.3(6) . . . . ?
C9 C17 C18 N1 99.2(5) . . . . ?
C24 C19 C20 C21 -0.3(8) . . . . ?
N1 C19 C20 C21 179.0(5) . . . . ?
C19 C20 C21 C22 1.3(9) . . . . ?
C20 C21 C22 C23 -0.9(8) . . . . ?
C20 C21 C22 C25 177.8(5) . . . . ?
C21 C22 C23 C24 -0.4(9) . . . . ?
C25 C22 C23 C24 -179.1(5) . . . . ?
C22 C23 C24 C19 1.3(9) . . . . ?
C20 C19 C24 C23 -1.0(8) . . . . ?
N1 C19 C24 C23 179.7(4) . . . . ?
O1 C18 N1 C19 -1.1(8) . . . . ?
C17 C18 N1 C19 -179.5(4) . . . . ?
C20 C19 N1 C18 25.1(8) . . . . ?
C24 C19 N1 C18 -155.6(5) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.063
