# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 2007817'
loop_
_audit_author_name
_audit_author_address
'Li Yongxin'
;NTU
Singapore
;
_audit_update_record             
;
2020-06-03 deposited with the CCDC.	2022-02-14 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            'C12 H12 F2 N2 O3'
_chemical_formula_weight         270.24

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                   7.6940(11)
_cell_length_b                   9.3007(14)
_cell_length_c                   9.6264(13)
_cell_angle_alpha                112.726(5)
_cell_angle_beta                 100.067(5)
_cell_angle_gamma                90.297(6)
_cell_volume                     623.59(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    304(2)
_cell_measurement_reflns_used    9921
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      27.55

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      304(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            18902
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.740
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measured_fraction_theta_full 0.883
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_Laue_measured_fraction_full 0.883
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_point_group_measured_fraction_full 0.883
_reflns_number_total             2503
_reflns_number_gt                1877
_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 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'
_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)+(0.2000P)²] 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         2503
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1892
_refine_ls_R_factor_gt           0.1660
_refine_ls_wR_factor_ref         0.4786
_refine_ls_wR_factor_gt          0.4397
_refine_ls_goodness_of_fit_ref   2.159
_refine_ls_restrained_S_all      2.159
_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 -0.0861(5) 0.7244(4) -0.1806(5) 0.0503(11) Uani 1 1 d . . . . .
N2 N 0.8331(5) 1.0789(5) 0.5910(5) 0.0544(12) Uani 1 1 d . . . . .
O1 O 0.1974(6) 0.8752(5) -0.0276(6) 0.0783(14) Uani 1 1 d . . . . .
O2 O 0.8488(7) 1.2204(5) 0.6580(6) 0.0896(16) Uani 1 1 d . . . . .
O3 O 0.9140(5) 0.9916(5) 0.6380(5) 0.0663(12) Uani 1 1 d . . . . .
C1 C 0.0997(6) 0.7569(5) -0.1744(5) 0.0479(12) Uani 1 1 d . . . . .
H1 H 0.1093 0.7935 -0.2558 0.058 Uiso 1 1 calc R U . . .
C2 C 0.2215(6) 0.6206(5) -0.1911(5) 0.0481(12) Uani 1 1 d . . . . .
C3 C 0.3448(5) 0.6619(4) -0.0584(4) 0.0373(10) Uani 1 1 d . . . . .
H3 H 0.4238 0.5970 -0.0323 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3309(6) 0.8196(4) 0.0313(5) 0.0419(11) Uani 1 1 d . . . . .
C5 C 0.4635(5) 0.8850(5) 0.1723(5) 0.0402(11) Uani 1 1 d . . . . .
C6 C 0.4770(7) 1.0451(5) 0.2590(6) 0.0494(12) Uani 1 1 d . . . . .
H6 H 0.4031 1.1089 0.2257 0.059 Uiso 1 1 calc R U . . .
C7 C 0.5992(6) 1.1098(5) 0.3942(6) 0.0484(12) Uani 1 1 d . . . . .
H7 H 0.6106 1.2172 0.4515 0.058 Uiso 1 1 calc R U . . .
C8 C 0.7048(5) 1.0114(5) 0.4430(5) 0.0441(11) Uani 1 1 d . . . . .
C9 C 0.6961(6) 0.8545(6) 0.3596(6) 0.0494(12) Uani 1 1 d . . . . .
H9 H 0.7706 0.7917 0.3938 0.059 Uiso 1 1 calc R U . . .
C10 C 0.5735(6) 0.7893(5) 0.2217(5) 0.0477(12) Uani 1 1 d . . . . .
H10 H 0.5656 0.6823 0.1634 0.057 Uiso 1 1 calc R U . . .
C11 C -0.1810(8) 0.6234(6) -0.3314(7) 0.0668(15) Uani 1 1 d . . . . .
H11A H -0.1436 0.6531 -0.4073 0.100 Uiso 1 1 calc R U . . .
H11B H -0.3059 0.6332 -0.3362 0.100 Uiso 1 1 calc R U . . .
H11C H -0.1567 0.5169 -0.3509 0.100 Uiso 1 1 calc R U . . .
C12 C -0.1244(9) 0.6792(8) -0.0589(8) 0.0739(17) Uani 1 1 d . . . . .
H12A H -0.2365 0.7146 -0.0345 0.111 Uiso 1 1 calc R U . . .
H12B H -0.0331 0.7259 0.0307 0.111 Uiso 1 1 calc R U . . .
H12C H -0.1287 0.5674 -0.0930 0.111 Uiso 1 1 calc R U . . .
F1 F 0.1429(4) 0.4829(3) -0.2193(4) 0.0709(11) Uani 1 1 d . . . . .
F2 F 0.3130(5) 0.5947(4) -0.3060(4) 0.0804(12) 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
N1 C1 1.446(6) . ?
N1 C11 1.446(7) . ?
N1 C12 1.461(7) . ?
N2 O3 1.200(6) . ?
N2 O2 1.215(6) . ?
N2 C8 1.486(6) . ?
O1 C4 1.293(6) . ?
O1 C1 1.480(7) . ?
C1 C2 1.555(6) . ?
C2 F1 1.321(6) . ?
C2 F2 1.358(6) . ?
C2 C3 1.369(6) . ?
C3 C4 1.401(5) . ?
C4 C5 1.457(6) . ?
C5 C10 1.389(6) . ?
C5 C6 1.391(6) . ?
C6 C7 1.379(7) . ?
C7 C8 1.388(7) . ?
C8 C9 1.361(7) . ?
C9 C10 1.397(7) . ?

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 C11 113.8(4) . . ?
C1 N1 C12 114.9(4) . . ?
C11 N1 C12 113.1(5) . . ?
O3 N2 O2 123.8(4) . . ?
O3 N2 C8 118.6(4) . . ?
O2 N2 C8 117.5(4) . . ?
C4 O1 C1 111.9(4) . . ?
N1 C1 O1 115.8(4) . . ?
N1 C1 C2 117.4(4) . . ?
O1 C1 C2 99.2(4) . . ?
F1 C2 F2 105.2(4) . . ?
F1 C2 C3 107.8(4) . . ?
F2 C2 C3 106.5(4) . . ?
F1 C2 C1 116.5(4) . . ?
F2 C2 C1 112.0(4) . . ?
C3 C2 C1 108.3(3) . . ?
C2 C3 C4 107.8(3) . . ?
O1 C4 C3 112.0(4) . . ?
O1 C4 C5 133.4(4) . . ?
C3 C4 C5 114.5(4) . . ?
C10 C5 C6 120.0(4) . . ?
C10 C5 C4 120.9(4) . . ?
C6 C5 C4 119.1(4) . . ?
C7 C6 C5 120.4(4) . . ?
C6 C7 C8 118.6(4) . . ?
C9 C8 C7 122.3(4) . . ?
C9 C8 N2 118.5(4) . . ?
C7 C8 N2 119.2(4) . . ?
C8 C9 C10 119.0(4) . . ?
C5 C10 C9 119.7(4) . . ?

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
C11 N1 C1 O1 172.6(4) . . . . ?
C12 N1 C1 O1 -54.6(5) . . . . ?
C11 N1 C1 C2 -70.7(5) . . . . ?
C12 N1 C1 C2 62.1(6) . . . . ?
C4 O1 C1 N1 122.4(5) . . . . ?
C4 O1 C1 C2 -4.1(5) . . . . ?
N1 C1 C2 F1 4.1(6) . . . . ?
O1 C1 C2 F1 129.6(4) . . . . ?
N1 C1 C2 F2 125.2(4) . . . . ?
O1 C1 C2 F2 -109.3(4) . . . . ?
N1 C1 C2 C3 -117.6(5) . . . . ?
O1 C1 C2 C3 7.9(5) . . . . ?
F1 C2 C3 C4 -135.8(4) . . . . ?
F2 C2 C3 C4 111.7(4) . . . . ?
C1 C2 C3 C4 -9.0(5) . . . . ?
C1 O1 C4 C3 -1.1(6) . . . . ?
C1 O1 C4 C5 -178.4(4) . . . . ?
C2 C3 C4 O1 6.6(6) . . . . ?
C2 C3 C4 C5 -175.5(4) . . . . ?
O1 C4 C5 C10 167.6(5) . . . . ?
C3 C4 C5 C10 -9.8(6) . . . . ?
O1 C4 C5 C6 -11.4(8) . . . . ?
C3 C4 C5 C6 171.3(4) . . . . ?
C10 C5 C6 C7 0.0(7) . . . . ?
C4 C5 C6 C7 178.9(4) . . . . ?
C5 C6 C7 C8 -1.5(7) . . . . ?
C6 C7 C8 C9 2.3(7) . . . . ?
C6 C7 C8 N2 -178.1(4) . . . . ?
O3 N2 C8 C9 -6.0(6) . . . . ?
O2 N2 C8 C9 174.4(4) . . . . ?
O3 N2 C8 C7 174.3(4) . . . . ?
O2 N2 C8 C7 -5.2(6) . . . . ?
C7 C8 C9 C10 -1.6(7) . . . . ?
N2 C8 C9 C10 178.7(4) . . . . ?
C6 C5 C10 C9 0.7(7) . . . . ?
C4 C5 C10 C9 -178.2(4) . . . . ?
C8 C9 C10 C5 0.1(7) . . . . ?

_refine_diff_density_max         1.519
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.113

