# Electronic Supplementary Material (ESI) for ChemComm.
# 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_X
_database_code_depnum_ccdc_archive 'CCDC 1982943'
loop_
_audit_author_name
_audit_author_address
'Dong Zhang'
;College of Biotechnology and Pharmaceutical Engineering Nanjing Tech University
China
;
_audit_update_record             
;
2020-02-10 deposited with the CCDC.	2020-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 F2 N3 O2'
_chemical_formula_weight         303.27

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.7930(16)
_cell_length_b                   9.7180(19)
_cell_length_c                   10.297(2)
_cell_angle_alpha                99.54(3)
_cell_angle_beta                 107.52(3)
_cell_angle_gamma                109.15(3)
_cell_volume                     671.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.121
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2667
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.170
_diffrn_reflns_theta_max         25.391
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2474
_reflns_number_gt                1868
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²+0.1300P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2474
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1400
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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
N1 N 0.4808(3) 0.7694(2) 0.32171(19) 0.0435(5) Uani 1 1 d . . . . .
F1 F 0.6680(3) 0.8641(2) 0.08781(17) 0.0766(5) Uani 1 1 d . . . . .
O1 O 0.8761(3) 1.2074(2) 0.3385(2) 0.0735(6) Uani 1 1 d . . . . .
C1 C 0.5452(3) 0.7963(2) 0.4695(2) 0.0424(5) Uani 1 1 d . . . . .
F2 F 0.3717(2) 0.84289(18) 0.06052(15) 0.0687(5) Uani 1 1 d . . . . .
O2 O 0.9918(2) 1.22557(18) 0.56961(18) 0.0563(5) Uani 1 1 d . . . . .
N2 N 0.1867(3) 0.5571(2) 0.2473(2) 0.0530(5) Uani 1 1 d . . . . .
C2 C 0.4799(4) 0.7024(3) 0.5477(3) 0.0525(6) Uani 1 1 d . . . . .
H2B H 0.3763 0.6072 0.5035 0.063 Uiso 1 1 calc R U . . .
N3 N 0.3976(3) 0.5743(2) 0.1201(2) 0.0508(5) Uani 1 1 d . . . . .
C3 C 0.5747(4) 0.7561(3) 0.6929(3) 0.0596(7) Uani 1 1 d . . . . .
H3B H 0.5335 0.6962 0.7482 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7303(4) 0.8972(3) 0.7594(3) 0.0607(7) Uani 1 1 d . . . . .
H4A H 0.7914 0.9295 0.8582 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7962(4) 0.9903(3) 0.6829(2) 0.0521(6) Uani 1 1 d . . . . .
H5A H 0.9006 1.0849 0.7287 0.063 Uiso 1 1 calc R U . . .
C6 C 0.7028(3) 0.9398(2) 0.5343(2) 0.0410(5) Uani 1 1 d . . . . .
C7 C 0.7295(3) 1.0019(2) 0.4206(2) 0.0416(5) Uani 1 1 d . . . . .
C8 C 0.5959(3) 0.8963(2) 0.2949(2) 0.0423(5) Uani 1 1 d . . . . .
C9 C 0.8700(3) 1.1536(3) 0.4345(3) 0.0475(6) Uani 1 1 d . . . . .
C10 C 1.1355(4) 1.3762(3) 0.5972(3) 0.0671(8) Uani 1 1 d . . . . .
H10A H 1.2152 1.4175 0.6972 0.101 Uiso 1 1 calc R U . . .
H10B H 1.2173 1.3711 0.5446 0.101 Uiso 1 1 calc R U . . .
H10C H 1.0698 1.4405 0.5681 0.101 Uiso 1 1 calc R U . . .
C11 C 0.5632(4) 0.9184(3) 0.1505(2) 0.0528(6) Uani 1 1 d . . . . .
H11A H 0.6034 1.0274 0.1597 0.063 Uiso 1 1 calc R U . . .
C12 C 0.3461(3) 0.6259(2) 0.2223(2) 0.0426(5) Uani 1 1 d . . . . .
C13 C 0.0669(4) 0.4192(3) 0.1570(3) 0.0570(7) Uani 1 1 d . . . . .
H13A H -0.0453 0.3645 0.1710 0.068 Uiso 1 1 calc R U . . .
C14 C 0.1020(4) 0.3548(3) 0.0447(3) 0.0567(6) Uani 1 1 d . . . . .
H14A H 0.0154 0.2592 -0.0183 0.068 Uiso 1 1 calc R U . . .
C15 C 0.2690(4) 0.4369(3) 0.0296(3) 0.0559(6) Uani 1 1 d . . . . .
H15A H 0.2957 0.3963 -0.0467 0.067 Uiso 1 1 calc R U . . .


_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
N1 C8 1.392(3) . ?
N1 C1 1.400(3) . ?
N1 C12 1.419(3) . ?
F1 C11 1.360(3) . ?
O1 C9 1.199(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.404(3) . ?
F2 C11 1.359(3) . ?
O2 C9 1.332(3) . ?
O2 C10 1.440(3) . ?
N2 C12 1.328(3) . ?
N2 C13 1.332(3) . ?
C2 C3 1.370(4) . ?
C2 H2B 0.9300 . ?
N3 C12 1.316(3) . ?
N3 C15 1.343(3) . ?
C3 C4 1.384(4) . ?
C3 H3B 0.9300 . ?
C4 C5 1.371(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.441(3) . ?
C7 C8 1.364(3) . ?
C7 C9 1.472(3) . ?
C8 C11 1.495(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9800 . ?
C13 C14 1.365(4) . ?
C13 H13A 0.9300 . ?
C14 C15 1.356(4) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?

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
C8 N1 C1 107.82(18) . . ?
C8 N1 C12 127.74(18) . . ?
C1 N1 C12 123.55(18) . . ?
C2 C1 N1 129.4(2) . . ?
C2 C1 C6 122.3(2) . . ?
N1 C1 C6 108.30(18) . . ?
C9 O2 C10 116.3(2) . . ?
C12 N2 C13 114.8(2) . . ?
C3 C2 C1 117.1(2) . . ?
C3 C2 H2B 121.5 . . ?
C1 C2 H2B 121.5 . . ?
C12 N3 C15 114.9(2) . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3B 119.1 . . ?
C4 C3 H3B 119.1 . . ?
C5 C4 C3 121.5(2) . . ?
C5 C4 H4A 119.3 . . ?
C3 C4 H4A 119.3 . . ?
C4 C5 C6 118.5(2) . . ?
C4 C5 H5A 120.7 . . ?
C6 C5 H5A 120.7 . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.7(2) . . ?
C1 C6 C7 106.44(19) . . ?
C8 C7 C6 107.75(19) . . ?
C8 C7 C9 125.1(2) . . ?
C6 C7 C9 127.2(2) . . ?
C7 C8 N1 109.65(18) . . ?
C7 C8 C11 125.5(2) . . ?
N1 C8 C11 124.6(2) . . ?
O1 C9 O2 123.5(2) . . ?
O1 C9 C7 125.5(2) . . ?
O2 C9 C7 111.0(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
F2 C11 F1 106.3(2) . . ?
F2 C11 C8 111.9(2) . . ?
F1 C11 C8 111.5(2) . . ?
F2 C11 H11A 109.0 . . ?
F1 C11 H11A 109.0 . . ?
C8 C11 H11A 109.0 . . ?
N3 C12 N2 127.9(2) . . ?
N3 C12 N1 116.3(2) . . ?
N2 C12 N1 115.7(2) . . ?
N2 C13 C14 122.8(2) . . ?
N2 C13 H13A 118.6 . . ?
C14 C13 H13A 118.6 . . ?
C15 C14 C13 116.8(2) . . ?
C15 C14 H14A 121.6 . . ?
C13 C14 H14A 121.6 . . ?
N3 C15 C14 122.8(2) . . ?
N3 C15 H15A 118.6 . . ?
C14 C15 H15A 118.6 . . ?

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 N1 C1 C2 -178.3(2) . . . . ?
C12 N1 C1 C2 -8.3(4) . . . . ?
C8 N1 C1 C6 -0.8(2) . . . . ?
C12 N1 C1 C6 169.1(2) . . . . ?
N1 C1 C2 C3 177.8(2) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.4(4) . . . . ?
C3 C4 C5 C6 -0.2(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C4 C5 C6 C7 -179.4(2) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
N1 C1 C6 C5 -178.2(2) . . . . ?
C2 C1 C6 C7 179.2(2) . . . . ?
N1 C1 C6 C7 1.5(2) . . . . ?
C5 C6 C7 C8 178.0(3) . . . . ?
C1 C6 C7 C8 -1.7(2) . . . . ?
C5 C6 C7 C9 -3.8(4) . . . . ?
C1 C6 C7 C9 176.6(2) . . . . ?
C6 C7 C8 N1 1.2(3) . . . . ?
C9 C7 C8 N1 -177.1(2) . . . . ?
C6 C7 C8 C11 175.5(2) . . . . ?
C9 C7 C8 C11 -2.8(4) . . . . ?
C1 N1 C8 C7 -0.3(3) . . . . ?
C12 N1 C8 C7 -169.7(2) . . . . ?
C1 N1 C8 C11 -174.7(2) . . . . ?
C12 N1 C8 C11 15.9(4) . . . . ?
C10 O2 C9 O1 0.3(4) . . . . ?
C10 O2 C9 C7 -179.4(2) . . . . ?
C8 C7 C9 O1 5.4(4) . . . . ?
C6 C7 C9 O1 -172.5(2) . . . . ?
C8 C7 C9 O2 -174.8(2) . . . . ?
C6 C7 C9 O2 7.2(3) . . . . ?
C7 C8 C11 F2 -146.3(2) . . . . ?
N1 C8 C11 F2 27.2(3) . . . . ?
C7 C8 C11 F1 94.9(3) . . . . ?
N1 C8 C11 F1 -91.6(3) . . . . ?
C15 N3 C12 N2 1.6(4) . . . . ?
C15 N3 C12 N1 178.7(2) . . . . ?
C13 N2 C12 N3 0.2(4) . . . . ?
C13 N2 C12 N1 -176.8(2) . . . . ?
C8 N1 C12 N3 37.9(3) . . . . ?
C1 N1 C12 N3 -130.0(2) . . . . ?
C8 N1 C12 N2 -144.8(2) . . . . ?
C1 N1 C12 N2 47.4(3) . . . . ?
C12 N2 C13 C14 -1.7(4) . . . . ?
N2 C13 C14 C15 1.2(4) . . . . ?
C12 N3 C15 C14 -2.2(3) . . . . ?
C13 C14 C15 N3 0.8(4) . . . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.077



