# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_20210401a
_database_code_depnum_ccdc_archive 'CCDC 2080868'
loop_
_audit_author_name
_audit_author_address
'Wen Wan'
;Shanghai University
China
;
_audit_update_record             
;
2021-04-29 deposited with the CCDC.	2021-08-26 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H10 F2 N2 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         268.22

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   6.2592(3)
_cell_length_b                   14.9217(7)
_cell_length_c                   13.9603(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.929(2)
_cell_angle_gamma                90
_cell_volume                     1296.89(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      23.86
_cell_measurement_temperature    303.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
;
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7456

_exptl_special_details           
;
;

_diffrn_ambient_temperature      303.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           ?

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       'Bruker APEX-II CCD'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            14768
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2940
_reflns_number_gt                1744
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0963
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_gt          0.1573
_refine_ls_wR_factor_ref         0.1911
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0882P)²+0.3503P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.330
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.3139(4) 0.41846(12) 0.68323(16) 0.1087(7) Uani d . . . 1 . .
F F2 0.0011(4) 0.46152(15) 0.62261(12) 0.1199(9) Uani d . . . 1 . .
O O1 0.1632(4) 0.38717(17) 0.85097(17) 0.0941(7) Uani d . . . 1 . .
O O2 -0.1621(3) 0.41731(14) 0.77660(15) 0.0854(6) Uani d . . . 1 . .
O O3 0.1703(3) 0.68363(12) 0.80901(13) 0.0745(6) Uani d . . . 1 . .
H H3A 0.104(5) 0.7030(12) 0.850(2) 0.112 Uiso calc U . R 1 . .
N N1 0.8775(4) 0.76607(18) 0.43554(18) 0.0895(8) Uani d . . . 1 . .
N N3 0.1182(3) 0.59486(13) 0.79316(13) 0.0556(5) Uani d . . . 1 . .
C C1 0.3500(3) 0.60641(15) 0.65983(14) 0.0488(5) Uani d . . . 1 . .
C C2 0.2939(4) 0.6133(2) 0.56177(15) 0.0667(7) Uani d . . . 1 . .
H H2 0.163835 0.589705 0.534784 0.08 Uiso calc U . R 1 . .
C C3 0.4290(5) 0.6547(2) 0.50355(17) 0.0723(8) Uani d . . . 1 . .
H H3 0.39032 0.659077 0.437584 0.087 Uiso calc U . R 1 . .
C C4 0.6208(4) 0.68957(16) 0.54336(16) 0.0579(6) Uani d . . . 1 . .
C C5 0.6795(4) 0.68296(17) 0.64115(17) 0.0616(6) Uani d . . . 1 . .
H H5 0.810183 0.706254 0.667788 0.074 Uiso calc U . R 1 . .
C C6 0.5443(4) 0.64185(17) 0.69892(16) 0.0587(6) Uani d . . . 1 . .
H H6 0.583501 0.637739 0.764874 0.07 Uiso calc U . R 1 . .
C C7 0.7622(5) 0.73275(18) 0.48277(18) 0.0689(7) Uani d . . . 1 . .
C C8 0.2042(3) 0.56167(15) 0.72222(14) 0.0501(5) Uani d . . . 1 . .
C C9 0.1403(5) 0.46596(18) 0.70326(18) 0.0655(7) Uani d . . . 1 . .
C C10 0.0459(5) 0.41838(18) 0.7869(2) 0.0677(7) Uani d . . . 1 . .
C C11 -0.2643(5) 0.3744(3) 0.8546(3) 0.0991(11) Uani d . . . 1 . .
H H11A -0.175364 0.325282 0.881047 0.119 Uiso calc U . R 1 . .
H H11B -0.402572 0.350148 0.829436 0.119 Uiso calc U . R 1 . .
C C12 -0.2937(8) 0.4396(3) 0.9307(3) 0.1272(15) Uani d . . . 1 . .
H H12A -0.370635 0.490698 0.903255 0.191 Uiso calc U . R 1 . .
H H12B -0.15591 0.458327 0.960563 0.191 Uiso calc U . R 1 . .
H H12C -0.373868 0.41249 0.978073 0.191 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C9 . 1.351(3) ?
F2 C9 . 1.352(3) ?
O1 C10 . 1.192(3) ?
O2 C10 . 1.295(3) ?
O2 C11 . 1.466(3) ?
O3 N3 . 1.377(2) ?
O3 H3A . 0.79(4) ?
N1 C7 . 1.141(3) ?
N3 C8 . 1.275(3) ?
C1 C2 . 1.382(3) ?
C1 C6 . 1.386(3) ?
C1 C8 . 1.484(3) ?
C2 C3 . 1.379(3) ?
C2 H2 . 0.93 ?
C3 C4 . 1.372(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.380(3) ?
C4 C7 . 1.438(3) ?
C5 C6 . 1.373(3) ?
C5 H5 . 0.93 ?
C6 H6 . 0.93 ?
C8 C9 . 1.499(3) ?
C9 C10 . 1.536(4) ?
C11 C12 . 1.466(5) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 O2 C11 . . 115.7(2) ?
N3 O3 H3A . . 109.5 ?
C8 N3 O3 . . 112.75(18) ?
C2 C1 C6 . . 119.0(2) ?
C2 C1 C8 . . 120.4(2) ?
C6 C1 C8 . . 120.58(18) ?
C3 C2 C1 . . 120.6(2) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
C4 C3 C2 . . 119.7(2) ?
C4 C3 H3 . . 120.1 ?
C2 C3 H3 . . 120.1 ?
C3 C4 C5 . . 120.4(2) ?
C3 C4 C7 . . 119.8(2) ?
C5 C4 C7 . . 119.8(2) ?
C6 C5 C4 . . 119.7(2) ?
C6 C5 H5 . . 120.1 ?
C4 C5 H5 . . 120.1 ?
C5 C6 C1 . . 120.6(2) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
N1 C7 C4 . . 178.7(3) ?
N3 C8 C1 . . 128.0(2) ?
N3 C8 C9 . . 112.39(19) ?
C1 C8 C9 . . 119.60(18) ?
F1 C9 F2 . . 105.4(2) ?
F1 C9 C8 . . 109.3(2) ?
F2 C9 C8 . . 109.3(2) ?
F1 C9 C10 . . 107.2(2) ?
F2 C9 C10 . . 110.2(2) ?
C8 C9 C10 . . 115.00(19) ?
O1 C10 O2 . . 127.8(3) ?
O1 C10 C9 . . 119.7(3) ?
O2 C10 C9 . . 112.5(3) ?
O2 C11 C12 . . 110.2(3) ?
O2 C11 H11A . . 109.6 ?
C12 C11 H11A . . 109.6 ?
O2 C11 H11B . . 109.6 ?
C12 C11 H11B . . 109.6 ?
H11A C11 H11B . . 108.1 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 0.0(4) ?
C8 C1 C2 C3 . . . . -180.0(2) ?
C1 C2 C3 C4 . . . . -0.1(4) ?
C2 C3 C4 C5 . . . . 0.3(4) ?
C2 C3 C4 C7 . . . . 179.9(3) ?
C3 C4 C5 C6 . . . . -0.5(4) ?
C7 C4 C5 C6 . . . . 179.9(2) ?
C4 C5 C6 C1 . . . . 0.4(4) ?
C2 C1 C6 C5 . . . . -0.2(4) ?
C8 C1 C6 C5 . . . . 179.8(2) ?
O3 N3 C8 C1 . . . . 1.2(3) ?
O3 N3 C8 C9 . . . . -178.0(2) ?
C2 C1 C8 N3 . . . . -120.5(3) ?
C6 C1 C8 N3 . . . . 59.6(3) ?
C2 C1 C8 C9 . . . . 58.6(3) ?
C6 C1 C8 C9 . . . . -121.3(2) ?
N3 C8 C9 F1 . . . . -138.3(2) ?
C1 C8 C9 F1 . . . . 42.4(3) ?
N3 C8 C9 F2 . . . . 106.8(2) ?
C1 C8 C9 F2 . . . . -72.4(3) ?
N3 C8 C9 C10 . . . . -17.7(3) ?
C1 C8 C9 C10 . . . . 163.0(2) ?
C11 O2 C10 O1 . . . . 1.7(5) ?
C11 O2 C10 C9 . . . . -178.9(2) ?
F1 C9 C10 O1 . . . . 39.2(3) ?
F2 C9 C10 O1 . . . . 153.4(3) ?
C8 C9 C10 O1 . . . . -82.5(3) ?
F1 C9 C10 O2 . . . . -140.2(2) ?
F2 C9 C10 O2 . . . . -26.1(3) ?
C8 C9 C10 O2 . . . . 98.0(3) ?
C10 O2 C11 C12 . . . . 87.4(4) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3A N1 4_476 0.79 2.00 2.777(3) 165.8 ?

