# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2049223'
loop_
_audit_author_name
_audit_author_address
'Raviteja Seera'
;IISc Bangalore
India
;
_audit_update_record             
;
2020-12-09 deposited with the CCDC.	2021-04-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 F N2 O2'
_chemical_formula_weight         258.25

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'

_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                   7.4017(4)
_cell_length_b                   9.1653(4)
_cell_length_c                   9.6034(4)
_cell_angle_alpha                97.121(2)
_cell_angle_beta                 98.953(2)
_cell_angle_gamma                106.990(3)
_cell_volume                     605.48(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2784
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10395
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -9
_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       12
_diffrn_reflns_theta_min         2.362
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2784
_reflns_number_gt                2452
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1253P)²+0.3173P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.2021
_refine_ls_wR_factor_gt          0.1959
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.005

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 0.0971(2) 0.45172(16) 0.85238(15) 0.0420(4) Uani 1 1 d . . . . .
O2 O -0.0659(3) 0.86417(16) 0.62659(16) 0.0494(4) Uani 1 1 d . . . . .
N1 N -0.0294(3) 0.62861(18) 0.76426(17) 0.0377(4) Uani 1 1 d . . . . .
N2 N -0.0733(3) 0.8037(2) 0.39128(19) 0.0426(4) Uani 1 1 d . . . . .
F1 F 0.0066(3) 0.8443(2) 1.0080(2) 0.0756(5) Uani 1 1 d . . . . .
H1A H -0.018(5) 0.737(4) 0.771(3) 0.069(9) Uiso 1 1 d . . . . .
H2B H -0.026(4) 0.897(4) 0.383(3) 0.053(7) Uiso 1 1 d . . . . .
H2A H -0.082(4) 0.736(4) 0.326(3) 0.056(8) Uiso 1 1 d . . . . .
C4 C -0.1931(3) 0.5966(2) 0.51777(19) 0.0326(4) Uani 1 1 d . . . . .
C5 C -0.1577(3) 0.5329(2) 0.6405(2) 0.0340(4) Uani 1 1 d . . . . .
C6 C -0.2527(3) 0.3771(2) 0.6390(2) 0.0410(5) Uani 1 1 d . . . . .
H6 H -0.231502 0.334615 0.720675 0.049 Uiso 1 1 calc R U . . .
C3 C -0.3228(3) 0.5018(2) 0.3968(2) 0.0375(4) Uani 1 1 d . . . . .
H3 H -0.348794 0.543995 0.315636 0.045 Uiso 1 1 calc R U . . .
C8 C 0.0919(3) 0.5843(2) 0.85855(19) 0.0342(4) Uani 1 1 d . . . . .
C7 C -0.1040(3) 0.7657(2) 0.5161(2) 0.0347(4) Uani 1 1 d . . . . .
C9 C 0.2298(3) 0.7125(2) 0.97159(19) 0.0366(4) Uani 1 1 d . . . . .
C10 C 0.1843(3) 0.8344(2) 1.0418(2) 0.0442(5) Uani 1 1 d . . . . .
C1 C -0.3782(3) 0.2853(2) 0.5167(3) 0.0459(5) Uani 1 1 d . . . . .
H1 H -0.439595 0.181042 0.516386 0.055 Uiso 1 1 calc R U . . .
C2 C -0.4135(3) 0.3467(2) 0.3949(2) 0.0442(5) Uani 1 1 d . . . . .
H2 H -0.497367 0.284259 0.312593 0.053 Uiso 1 1 calc R U . . .
C14 C 0.4163(3) 0.7091(3) 1.0120(2) 0.0485(5) Uani 1 1 d . . . . .
H14 H 0.451497 0.628019 0.968436 0.058 Uiso 1 1 calc R U . . .
C11 C 0.3145(4) 0.9469(3) 1.1490(3) 0.0584(7) Uani 1 1 d . . . . .
H11 H 0.277754 1.024925 1.196511 0.070 Uiso 1 1 calc R U . . .
C13 C 0.5513(4) 0.8238(4) 1.1161(3) 0.0612(7) Uani 1 1 d . . . . .
H13 H 0.676934 0.821213 1.139592 0.073 Uiso 1 1 calc R U . . .
C12 C 0.4992(4) 0.9418(3) 1.1847(3) 0.0625(7) Uani 1 1 d . . . . .
H12 H 0.589501 1.018260 1.255283 0.075 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
O1 C8 1.222(2) . ?
O2 C7 1.241(2) . ?
N1 C8 1.357(2) . ?
N1 C5 1.409(2) . ?
N2 C7 1.324(3) . ?
F1 C10 1.337(3) . ?
C4 C3 1.393(3) . ?
C4 C5 1.401(3) . ?
C4 C7 1.499(2) . ?
C5 C6 1.392(3) . ?
C6 C1 1.382(3) . ?
C3 C2 1.380(3) . ?
C8 C9 1.496(3) . ?
C9 C14 1.385(3) . ?
C9 C10 1.386(3) . ?
C10 C11 1.378(3) . ?
C1 C2 1.381(3) . ?
C14 C13 1.385(4) . ?
C11 C12 1.373(4) . ?
C13 C12 1.378(4) . ?

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 C5 125.72(16) . . ?
C3 C4 C5 118.94(17) . . ?
C3 C4 C7 119.23(16) . . ?
C5 C4 C7 121.73(16) . . ?
C6 C5 C4 119.44(18) . . ?
C6 C5 N1 121.21(17) . . ?
C4 C5 N1 119.34(16) . . ?
C1 C6 C5 120.32(19) . . ?
C2 C3 C4 121.36(19) . . ?
O1 C8 N1 124.29(18) . . ?
O1 C8 C9 120.51(17) . . ?
N1 C8 C9 115.16(16) . . ?
O2 C7 N2 122.29(17) . . ?
O2 C7 C4 120.92(17) . . ?
N2 C7 C4 116.77(16) . . ?
C14 C9 C10 116.9(2) . . ?
C14 C9 C8 118.30(18) . . ?
C10 C9 C8 124.80(19) . . ?
F1 C10 C11 117.4(2) . . ?
F1 C10 C9 119.9(2) . . ?
C11 C10 C9 122.7(2) . . ?
C2 C1 C6 120.72(19) . . ?
C1 C2 C3 119.18(19) . . ?
C9 C14 C13 121.3(2) . . ?
C12 C11 C10 118.9(2) . . ?
C12 C13 C14 119.9(2) . . ?
C11 C12 C13 120.2(2) . . ?

_refine_diff_density_max         1.528
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.071

