# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2093218'
loop_
_audit_author_name
_audit_author_address
'Qingxia Yao'
;Liaocheng University
China
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 F2 N3 O'
_chemical_formula_weight         327.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   9.0804(5)
_cell_length_b                   11.6360(9)
_cell_length_c                   15.8656(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1676.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6242
_cell_measurement_theta_min      4.713
_cell_measurement_theta_max      71.307

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.823
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6242
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.713
_diffrn_reflns_theta_max         71.307
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_point_group_measured_fraction_full 0.907
_reflns_number_total             2879
_reflns_number_gt                2062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.568
_reflns_Friedel_fraction_max     0.757
_reflns_Friedel_fraction_full    0.782

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0480P)²+0.0609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0066(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 542 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.55(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2879
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0490
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.1850(3) -0.0234(3) 0.52015(17) 0.0710(8) Uani 1 1 d . . . . .
N1 N -0.0205(3) 0.0370(3) 0.45335(19) 0.0514(7) Uani 1 1 d . . . . .
C2 C -0.0272(4) 0.0234(3) 0.6032(2) 0.0566(9) Uani 1 1 d . . . . .
F2 F -0.0061(3) 0.2313(2) 0.35669(17) 0.0963(9) Uani 1 1 d . . . . .
N2 N 0.1909(3) 0.3545(3) 0.5422(2) 0.0657(9) Uani 1 1 d . . . . .
C1 C 0.0581(4) 0.0098(3) 0.5231(2) 0.0529(9) Uani 1 1 d . . . . .
C13 C 0.0428(4) 0.0362(3) 0.3718(2) 0.0553(9) Uani 1 1 d . . . . .
C7 C -0.0451(4) 0.1326(4) 0.6379(2) 0.0579(9) Uani 1 1 d . . . . .
N3 N 0.0602(3) 0.4075(3) 0.5476(3) 0.0710(10) Uani 1 1 d . . . . .
F1 F 0.0917(4) -0.1613(2) 0.3808(2) 0.1086(11) Uani 1 1 d . . . . .
C18 C 0.0484(4) 0.1329(4) 0.3230(3) 0.0681(11) Uani 1 1 d . . . . .
C10 C 0.1669(4) 0.2498(4) 0.5723(2) 0.0601(10) Uani 1 1 d . . . . .
H10 H 0.2402 0.1917 0.5753 0.072 Uiso 1 1 calc R U . . .
C9 C 0.0209(4) 0.2347(3) 0.5991(2) 0.0561(9) Uani 1 1 d . . . . .
C11 C -0.0420(4) 0.3397(4) 0.5816(3) 0.0698(11) Uani 1 1 d . . . . .
H11 H -0.1416 0.3603 0.5919 0.084 Uiso 1 1 calc R U . . .
C3 C -0.0887(5) -0.0742(4) 0.6417(3) 0.0762(13) Uani 1 1 d . . . . .
C17 C 0.1054(5) 0.1340(6) 0.2427(3) 0.0937(17) Uani 1 1 d . . . . .
H17 H 0.1031 0.2018 0.2093 0.112 Uiso 1 1 calc R U . . .
C15 C 0.1640(7) -0.0647(6) 0.2590(4) 0.1047(19) Uani 1 1 d . . . . .
H15 H 0.2064 -0.1334 0.2375 0.126 Uiso 1 1 calc R U . . .
C6 C -0.1279(5) 0.1431(5) 0.7120(3) 0.0842(14) Uani 1 1 d . . . . .
H6 H -0.1421 0.2165 0.7369 0.101 Uiso 1 1 calc R U . . .
C4 C -0.1686(7) -0.0605(6) 0.7143(4) 0.104(2) Uani 1 1 d . . . . .
H4 H -0.2104 -0.1260 0.7410 0.125 Uiso 1 1 calc R U . . .
C14 C 0.1008(5) -0.0631(4) 0.3368(3) 0.0742(13) Uani 1 1 d . . . . .
C16 C 0.1658(6) 0.0340(7) 0.2122(3) 0.107(2) Uani 1 1 d . . . . .
H16 H 0.2094 0.0335 0.1578 0.128 Uiso 1 1 calc R U . . .
C8 C -0.0671(7) -0.1918(4) 0.6032(4) 0.111(2) Uani 1 1 d . . . . .
H8A H -0.1132 -0.2499 0.6392 0.166 Uiso 1 1 calc R U . . .
H8B H 0.0385 -0.2079 0.5982 0.166 Uiso 1 1 calc R U . . .
H8C H -0.1124 -0.1937 0.5471 0.166 Uiso 1 1 calc R U . . .
C5 C -0.1892(6) 0.0458(7) 0.7490(3) 0.108(2) Uani 1 1 d . . . . .
H5 H -0.2459 0.0534 0.7990 0.130 Uiso 1 1 calc R U . . .
C12 C 0.0440(6) 0.5251(4) 0.5155(4) 0.109(2) Uani 1 1 d . . . . .
H12A H -0.0567 0.5520 0.5256 0.163 Uiso 1 1 calc R U . . .
H12B H 0.0644 0.5261 0.4549 0.163 Uiso 1 1 calc R U . . .
H12C H 0.1136 0.5758 0.5446 0.163 Uiso 1 1 calc R U . . .
H1 H -0.109(4) 0.075(3) 0.458(2) 0.058(11) Uiso 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
O1 C1 1.216(4) . ?
N1 C1 1.355(4) . ?
N1 C13 1.416(5) . ?
C2 C7 1.395(5) . ?
C2 C3 1.406(5) . ?
C2 C1 1.497(5) . ?
F2 C18 1.357(5) . ?
N2 C10 1.327(5) . ?
N2 N3 1.340(4) . ?
C13 C18 1.367(6) . ?
C13 C14 1.386(5) . ?
C7 C6 1.400(6) . ?
C7 C9 1.465(5) . ?
N3 C11 1.331(5) . ?
N3 C12 1.468(5) . ?
F1 C14 1.343(5) . ?
C18 C17 1.376(6) . ?
C10 C9 1.404(5) . ?
C9 C11 1.377(6) . ?
C3 C4 1.371(7) . ?
C3 C8 1.511(7) . ?
C17 C16 1.374(8) . ?
C15 C14 1.361(7) . ?
C15 C16 1.368(9) . ?
C6 C5 1.392(7) . ?
C4 C5 1.367(8) . ?

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
C1 N1 C13 122.1(3) . . ?
C7 C2 C3 121.3(4) . . ?
C7 C2 C1 119.5(3) . . ?
C3 C2 C1 119.3(4) . . ?
C10 N2 N3 104.7(3) . . ?
O1 C1 N1 122.8(4) . . ?
O1 C1 C2 123.8(3) . . ?
N1 C1 C2 113.4(3) . . ?
C18 C13 C14 116.4(4) . . ?
C18 C13 N1 121.8(3) . . ?
C14 C13 N1 121.8(4) . . ?
C2 C7 C6 118.2(4) . . ?
C2 C7 C9 121.7(3) . . ?
C6 C7 C9 120.1(4) . . ?
C11 N3 N2 111.8(3) . . ?
C11 N3 C12 128.6(4) . . ?
N2 N3 C12 119.7(4) . . ?
F2 C18 C13 117.3(3) . . ?
F2 C18 C17 119.6(5) . . ?
C13 C18 C17 123.1(5) . . ?
N2 C10 C9 112.3(4) . . ?
C11 C9 C10 102.6(4) . . ?
C11 C9 C7 129.4(3) . . ?
C10 C9 C7 128.0(4) . . ?
N3 C11 C9 108.6(3) . . ?
C4 C3 C2 118.8(5) . . ?
C4 C3 C8 121.0(5) . . ?
C2 C3 C8 120.3(4) . . ?
C16 C17 C18 117.9(6) . . ?
C14 C15 C16 119.0(5) . . ?
C5 C6 C7 119.9(5) . . ?
C5 C4 C3 121.1(5) . . ?
F1 C14 C15 119.1(5) . . ?
F1 C14 C13 118.5(4) . . ?
C15 C14 C13 122.4(5) . . ?
C15 C16 C17 121.0(5) . . ?
C4 C5 C6 120.8(5) . . ?

_refine_diff_density_max         0.111
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2093220'
loop_
_audit_author_name
_audit_author_address
'Qingxia Yao'
;Liaocheng University
China
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2021-12-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 F2 N2 O'
_chemical_formula_weight         338.35

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/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                   7.8673(7)
_cell_length_b                   8.8248(8)
_cell_length_c                   24.008(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.367(2)
_cell_angle_gamma                90
_cell_volume                     1664.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8019
_cell_measurement_theta_min      2.459
_cell_measurement_theta_max      25.018

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8019
_diffrn_reflns_av_unetI/netI     0.1073
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.459
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2933
_reflns_number_gt                1629
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1143P)²+0.1050P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2933
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.2092
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.003
_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
N3 N 0.6290(4) 0.0601(3) -0.06513(13) 0.0381(9) Uani 1 1 d . . . . .
N1 N 0.4201(4) 0.2249(4) 0.12135(14) 0.0412(9) Uani 1 1 d . . . . .
C3 C 0.7801(5) 0.1084(4) 0.08377(17) 0.0376(10) Uani 1 1 d . . . . .
C2 C 0.7211(5) 0.1679(4) 0.13281(16) 0.0380(10) Uani 1 1 d . . . . .
C1 C 0.5772(5) 0.2802(5) 0.13329(16) 0.0422(10) Uani 1 1 d . . . . .
C15 C 0.2765(5) 0.3184(5) 0.12651(18) 0.0432(11) Uani 1 1 d . . . . .
C12 C 0.7081(5) 0.1485(4) 0.02726(16) 0.0354(9) Uani 1 1 d . . . . .
F2 F 0.2232(4) 0.3344(3) 0.03095(12) 0.0771(10) Uani 1 1 d . . . . .
C11 C 0.6879(5) 0.0372(4) -0.01307(17) 0.0386(10) Uani 1 1 d . . . . .
H11 H 0.7181 -0.0613 -0.0028 0.046 Uiso 1 1 calc R U . . .
C7 C 0.7962(5) 0.1278(5) 0.18467(17) 0.0457(11) Uani 1 1 d . . . . .
C10 C 0.5796(5) 0.1996(4) -0.07991(16) 0.0410(10) Uani 1 1 d . . . . .
F3 F 0.3146(4) 0.3056(4) 0.22362(12) 0.0891(11) Uani 1 1 d . . . . .
C13 C 0.6570(5) 0.2928(4) 0.01093(17) 0.0408(10) Uani 1 1 d . . . . .
H13 H 0.6676 0.3730 0.0360 0.049 Uiso 1 1 calc R U . . .
O1 O 0.6026(4) 0.4116(3) 0.14714(13) 0.0560(9) Uani 1 1 d . . . . .
C14 C 0.5911(5) 0.3168(4) -0.04213(17) 0.0425(11) Uani 1 1 d . . . . .
H14 H 0.5536 0.4131 -0.0528 0.051 Uiso 1 1 calc R U . . .
C4 C 0.9177(5) 0.0086(5) 0.0878(2) 0.0518(12) Uani 1 1 d . . . . .
H4 H 0.9602 -0.0305 0.0554 0.062 Uiso 1 1 calc R U . . .
C6 C 0.9321(6) 0.0260(5) 0.1861(2) 0.0589(13) Uani 1 1 d . . . . .
H6 H 0.9833 -0.0023 0.2204 0.071 Uiso 1 1 calc R U . . .
C16 C 0.1799(6) 0.3741(5) 0.0821(2) 0.0511(12) Uani 1 1 d . . . . .
C17 C 0.0436(6) 0.4686(5) 0.0875(3) 0.0698(15) Uani 1 1 d . . . . .
H17 H -0.0200 0.5028 0.0562 0.084 Uiso 1 1 calc R U . . .
C8 C 0.7369(7) 0.1894(6) 0.23822(18) 0.0662(14) Uani 1 1 d . . . . .
H8A H 0.7831 0.2891 0.2445 0.099 Uiso 1 1 calc R U . . .
H8B H 0.7748 0.1242 0.2685 0.099 Uiso 1 1 calc R U . . .
H8C H 0.6148 0.1945 0.2361 0.099 Uiso 1 1 calc R U . . .
C20 C 0.2270(6) 0.3640(5) 0.1778(2) 0.0578(13) Uani 1 1 d . . . . .
C5 C 0.9915(6) -0.0329(6) 0.1387(2) 0.0626(14) Uani 1 1 d . . . . .
H5 H 1.0818 -0.1010 0.1408 0.075 Uiso 1 1 calc R U . . .
C9 C 0.5122(7) 0.2204(5) -0.13891(18) 0.0620(14) Uani 1 1 d . . . . .
H9A H 0.6016 0.2023 -0.1636 0.093 Uiso 1 1 calc R U . . .
H9B H 0.4708 0.3221 -0.1439 0.093 Uiso 1 1 calc R U . . .
H9C H 0.4208 0.1503 -0.1470 0.093 Uiso 1 1 calc R U . . .
C18 C 0.0027(7) 0.5118(6) 0.1394(3) 0.0766(17) Uani 1 1 d . . . . .
H18 H -0.0872 0.5785 0.1434 0.092 Uiso 1 1 calc R U . . .
C19 C 0.0923(7) 0.4583(6) 0.1854(3) 0.0774(17) Uani 1 1 d . . . . .
H19 H 0.0627 0.4850 0.2211 0.093 Uiso 1 1 calc R U . . .
H1 H 0.409(7) 0.124(6) 0.102(2) 0.089(17) Uiso 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
N3 C11 1.323(5) . ?
N3 C10 1.333(5) . ?
N1 C1 1.344(5) . ?
N1 C15 1.411(5) . ?
C3 C2 1.394(5) . ?
C3 C4 1.394(6) . ?
C3 C12 1.482(5) . ?
C2 C7 1.392(5) . ?
C2 C1 1.506(6) . ?
C1 O1 1.220(4) . ?
C15 C16 1.365(6) . ?
C15 C20 1.374(6) . ?
C12 C11 1.382(5) . ?
C12 C13 1.386(5) . ?
F2 C16 1.339(5) . ?
C7 C6 1.395(6) . ?
C7 C8 1.496(6) . ?
C10 C14 1.375(5) . ?
C10 C9 1.495(5) . ?
F3 C20 1.364(5) . ?
C13 C14 1.363(5) . ?
C4 C5 1.372(6) . ?
C6 C5 1.359(6) . ?
C16 C17 1.371(6) . ?
C17 C18 1.358(7) . ?
C20 C19 1.368(7) . ?
C18 C19 1.360(8) . ?

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
C11 N3 C10 118.3(3) . . ?
C1 N1 C15 120.0(3) . . ?
C2 C3 C4 118.4(4) . . ?
C2 C3 C12 123.7(3) . . ?
C4 C3 C12 117.8(4) . . ?
C7 C2 C3 121.0(4) . . ?
C7 C2 C1 116.1(4) . . ?
C3 C2 C1 122.9(3) . . ?
O1 C1 N1 122.5(4) . . ?
O1 C1 C2 121.1(4) . . ?
N1 C1 C2 116.2(4) . . ?
C16 C15 C20 115.0(4) . . ?
C16 C15 N1 123.6(4) . . ?
C20 C15 N1 121.4(4) . . ?
C11 C12 C13 115.8(4) . . ?
C11 C12 C3 119.6(3) . . ?
C13 C12 C3 124.6(3) . . ?
N3 C11 C12 125.0(4) . . ?
C2 C7 C6 118.1(4) . . ?
C2 C7 C8 122.6(4) . . ?
C6 C7 C8 119.3(4) . . ?
N3 C10 C14 120.8(4) . . ?
N3 C10 C9 116.6(4) . . ?
C14 C10 C9 122.6(4) . . ?
C14 C13 C12 119.7(4) . . ?
C13 C14 C10 120.4(4) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C6 C7 121.7(4) . . ?
F2 C16 C15 117.6(4) . . ?
F2 C16 C17 119.3(5) . . ?
C15 C16 C17 123.1(5) . . ?
C18 C17 C16 119.2(5) . . ?
F3 C20 C19 118.8(5) . . ?
F3 C20 C15 117.1(4) . . ?
C19 C20 C15 124.0(5) . . ?
C6 C5 C4 119.8(4) . . ?
C17 C18 C19 120.5(5) . . ?
C18 C19 C20 118.1(5) . . ?

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4

