# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_181213a_0m
_database_code_depnum_ccdc_archive 'CCDC 1953734'
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2019-09-16 deposited with the CCDC.	2019-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 F2 N2 O'
_chemical_formula_weight         286.28

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.471(13)
_cell_length_b                   8.149(14)
_cell_length_c                   13.09(2)
_cell_angle_alpha                91.378(19)
_cell_angle_beta                 105.627(19)
_cell_angle_gamma                115.663(17)
_cell_volume                     683(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1512
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      27.53

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3472
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2358
_reflns_number_gt                1889
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0565P)²+0.0774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2358
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1004
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1784(2) 0.44316(19) 0.44359(11) 0.0422(3) Uani 1 1 d . . .
C2 C 0.0335(2) 0.2681(2) 0.45461(13) 0.0524(4) Uani 1 1 d . . .
H2 H -0.0638 0.1835 0.3938 0.063 Uiso 1 1 calc R . .
C3 C 0.0357(3) 0.2226(2) 0.55414(14) 0.0565(4) Uani 1 1 d . . .
H3 H -0.0607 0.1069 0.5608 0.068 Uiso 1 1 calc R . .
C4 C 0.1811(3) 0.3477(2) 0.64663(14) 0.0580(4) Uani 1 1 d . . .
H4 H 0.1814 0.3139 0.7140 0.070 Uiso 1 1 calc R . .
C5 C 0.3220(3) 0.5183(2) 0.63877(13) 0.0557(4) Uani 1 1 d . . .
H5 H 0.4177 0.6009 0.7006 0.067 Uiso 1 1 calc R . .
C6 C 0.3230(2) 0.5702(2) 0.53677(12) 0.0444(4) Uani 1 1 d . . .
C7 C 0.4558(2) 0.7812(2) 0.43250(13) 0.0519(4) Uani 1 1 d . . .
H7 H 0.5481 0.8979 0.4247 0.062 Uiso 1 1 calc R . .
C8 C 0.3145(2) 0.6531(2) 0.33908(11) 0.0437(4) Uani 1 1 d . . .
C9 C 0.3123(3) 0.7075(2) 0.22871(13) 0.0526(4) Uani 1 1 d . . .
C10 C 0.1590(2) 0.7803(2) 0.18261(11) 0.0470(4) Uani 1 1 d . . .
C11 C 0.1994(3) 0.9555(2) 0.22375(12) 0.0525(4) Uani 1 1 d . . .
H11 H 0.3230 1.0273 0.2786 0.063 Uiso 1 1 calc R . .
C12 C 0.0601(3) 1.0260(2) 0.18513(12) 0.0534(4) Uani 1 1 d . . .
H12 H 0.0898 1.1438 0.2137 0.064 Uiso 1 1 calc R . .
C13 C -0.1233(3) 0.9193(2) 0.10366(12) 0.0515(4) Uani 1 1 d . . .
C14 C -0.1665(3) 0.7431(2) 0.06283(13) 0.0600(4) Uani 1 1 d . . .
H14 H -0.2905 0.6708 0.0084 0.072 Uiso 1 1 calc R . .
C15 C -0.0269(3) 0.6744(2) 0.10235(12) 0.0564(4) Uani 1 1 d . . .
H15 H -0.0580 0.5556 0.0747 0.068 Uiso 1 1 calc R . .
C16 C -0.2389(3) 1.1516(3) 0.10078(17) 0.0757(6) Uani 1 1 d . . .
H16A H -0.2374 1.1537 0.1744 0.114 Uiso 1 1 calc R . .
H16B H -0.3501 1.1755 0.0596 0.114 Uiso 1 1 calc R . .
H16C H -0.1079 1.2446 0.0969 0.114 Uiso 1 1 calc R . .
F1 F 0.27752(18) 0.55997(14) 0.16008(8) 0.0728(3) Uani 1 1 d . . .
F2 F 0.51125(16) 0.84021(15) 0.23795(9) 0.0730(3) Uani 1 1 d . . .
N1 N 0.17644(19) 0.48765(16) 0.34303(9) 0.0451(3) Uani 1 1 d . . .
N2 N 0.4629(2) 0.74325(18) 0.52978(10) 0.0544(4) Uani 1 1 d . . .
O1 O -0.27085(19) 0.97446(17) 0.05829(9) 0.0669(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
C1 N1 1.372(3) . ?
C1 C2 1.409(3) . ?
C1 C6 1.410(3) . ?
C2 C3 1.361(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.411(3) . ?
C5 H5 0.9300 . ?
C6 N2 1.367(3) . ?
C7 N2 1.310(3) . ?
C7 C8 1.410(3) . ?
C7 H7 0.9300 . ?
C8 N1 1.308(2) . ?
C8 C9 1.520(3) . ?
C9 F1 1.368(3) . ?
C9 F2 1.378(3) . ?
C9 C10 1.504(3) . ?
C10 C15 1.382(3) . ?
C10 C11 1.386(3) . ?
C11 C12 1.384(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 O1 1.363(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 O1 1.429(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
N1 C1 C2 119.80(14) . . ?
N1 C1 C6 121.11(16) . . ?
C2 C1 C6 119.10(16) . . ?
C3 C2 C1 120.07(16) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.87(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.50(17) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.04(16) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
N2 C6 C1 121.01(16) . . ?
N2 C6 C5 119.59(14) . . ?
C1 C6 C5 119.41(17) . . ?
N2 C7 C8 122.98(17) . . ?
N2 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
N1 C8 C7 122.33(16) . . ?
N1 C8 C9 117.43(13) . . ?
C7 C8 C9 120.19(17) . . ?
F1 C9 F2 105.51(15) . . ?
F1 C9 C10 110.70(16) . . ?
F2 C9 C10 109.37(18) . . ?
F1 C9 C8 108.90(16) . . ?
F2 C9 C8 107.16(13) . . ?
C10 C9 C8 114.75(13) . . ?
C15 C10 C11 118.44(16) . . ?
C15 C10 C9 121.76(18) . . ?
C11 C10 C9 119.76(16) . . ?
C12 C11 C10 121.53(16) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119.26(18) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
O1 C13 C12 124.59(18) . . ?
O1 C13 C14 115.71(16) . . ?
C12 C13 C14 119.70(16) . . ?
C15 C14 C13 120.44(17) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C10 120.63(19) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C8 N1 C1 116.37(13) . . ?
C7 N2 C6 116.18(13) . . ?
C13 O1 C16 118.04(15) . . ?

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
N1 C1 C2 C3 179.46(13) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 C5 0.7(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
N1 C1 C6 N2 1.5(2) . . . . ?
C2 C1 C6 N2 -178.31(13) . . . . ?
N1 C1 C6 C5 -179.12(13) . . . . ?
C2 C1 C6 C5 1.1(2) . . . . ?
C4 C5 C6 N2 178.83(14) . . . . ?
C4 C5 C6 C1 -0.6(2) . . . . ?
N2 C7 C8 N1 1.6(2) . . . . ?
N2 C7 C8 C9 178.95(14) . . . . ?
N1 C8 C9 F1 -40.3(2) . . . . ?
C7 C8 C9 F1 142.26(16) . . . . ?
N1 C8 C9 F2 -153.93(13) . . . . ?
C7 C8 C9 F2 28.59(18) . . . . ?
N1 C8 C9 C10 84.4(2) . . . . ?
C7 C8 C9 C10 -93.0(2) . . . . ?
F1 C9 C10 C15 19.74(19) . . . . ?
F2 C9 C10 C15 135.57(17) . . . . ?
C8 C9 C10 C15 -104.00(19) . . . . ?
F1 C9 C10 C11 -162.78(13) . . . . ?
F2 C9 C10 C11 -46.94(19) . . . . ?
C8 C9 C10 C11 73.5(2) . . . . ?
C15 C10 C11 C12 -1.0(2) . . . . ?
C9 C10 C11 C12 -178.58(14) . . . . ?
C10 C11 C12 C13 0.0(2) . . . . ?
C11 C12 C13 O1 -179.15(14) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
O1 C13 C14 C15 179.42(14) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C11 C10 C15 C14 1.3(2) . . . . ?
C9 C10 C15 C14 178.80(14) . . . . ?
C7 C8 N1 C1 -1.2(2) . . . . ?
C9 C8 N1 C1 -178.58(12) . . . . ?
C2 C1 N1 C8 179.49(13) . . . . ?
C6 C1 N1 C8 -0.3(2) . . . . ?
C8 C7 N2 C6 -0.4(2) . . . . ?
C1 C6 N2 C7 -1.1(2) . . . . ?
C5 C6 N2 C7 179.52(14) . . . . ?
C12 C13 O1 C16 -2.9(2) . . . . ?
C14 C13 O1 C16 177.11(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.975
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.032
