# 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_KA1004_0m
_database_code_depnum_ccdc_archive 'CCDC 2047903'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2020-12-03 deposited with the CCDC.	2021-06-10 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         'C13 H12 F N O4'
_chemical_formula_sum            'C13 H12 F N O4'
_chemical_formula_weight         265.24

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.7100(7)
_cell_length_b                   9.8223(10)
_cell_length_c                   16.1672(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1224.34(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5940
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.29

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4612
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11447
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         30.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3688
_reflns_number_gt                2579
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_max     0.989
_reflns_Friedel_fraction_full    0.996

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0598P)²+0.1181P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 871 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3688
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.008
_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
C1 C 0.6217(3) 0.4320(2) 0.47905(14) 0.0324(5) Uani 1 1 d . . . . .
C2 C 0.5848(4) 0.4542(3) 0.56220(16) 0.0410(6) Uani 1 1 d . . . . .
H2 H 0.543802 0.384484 0.595890 0.049 Uiso 1 1 calc R U . . .
C3 C 0.6115(4) 0.5844(3) 0.59282(16) 0.0446(7) Uani 1 1 d . . . . .
H3 H 0.588556 0.600166 0.648481 0.054 Uiso 1 1 calc R U . . .
C4 C 0.6704(3) 0.6927(3) 0.54530(16) 0.0403(6) Uani 1 1 d . . . . .
C5 C 0.7057(4) 0.6690(3) 0.46304(16) 0.0390(6) Uani 1 1 d . . . . .
H5 H 0.745612 0.739221 0.429446 0.047 Uiso 1 1 calc R U . . .
C6 C 0.6813(3) 0.5393(3) 0.43062(14) 0.0338(5) Uani 1 1 d . . . . .
C7 C 0.7137(4) 0.4896(3) 0.34719(15) 0.0391(6) Uani 1 1 d . . . . .
C8 C 0.6487(3) 0.3393(3) 0.34614(15) 0.0349(5) Uani 1 1 d . . . . .
C9 C 0.6966(5) 0.8315(3) 0.5835(2) 0.0574(8) Uani 1 1 d . . . . .
H9A H 0.640875 0.899156 0.549849 0.086 Uiso 1 1 calc R U . . .
H9B H 0.818417 0.850898 0.586919 0.086 Uiso 1 1 calc R U . . .
H9C H 0.647106 0.832749 0.637973 0.086 Uiso 1 1 calc R U . . .
C10 C 0.4931(4) 0.3277(3) 0.28741(15) 0.0389(6) Uani 1 1 d . . . . .
C11 C 0.1949(4) 0.3769(4) 0.2767(2) 0.0551(8) Uani 1 1 d . . . . .
H11A H 0.199964 0.448535 0.236432 0.083 Uiso 1 1 calc R U . . .
H11B H 0.098457 0.392098 0.313136 0.083 Uiso 1 1 calc R U . . .
H11C H 0.180719 0.291034 0.249156 0.083 Uiso 1 1 calc R U . . .
C12 C 0.5548(4) 0.1856(3) 0.46202(17) 0.0412(6) Uani 1 1 d . . . . .
C13 C 0.5464(5) 0.0691(3) 0.4020(2) 0.0582(8) Uani 1 1 d . . . . .
H13A H 0.473353 0.093511 0.356266 0.087 Uiso 1 1 calc R U . . .
H13B H 0.499474 -0.009520 0.429266 0.087 Uiso 1 1 calc R U . . .
H13C H 0.660877 0.048962 0.382198 0.087 Uiso 1 1 calc R U . . .
F1 F 0.7797(2) 0.25847(18) 0.31582(10) 0.0463(4) Uani 1 1 d . . . . .
O1 O 0.7807(3) 0.5414(2) 0.28822(12) 0.0599(6) Uani 1 1 d . . . . .
O2 O 0.3540(2) 0.3753(2) 0.32419(12) 0.0504(5) Uani 1 1 d . . . . .
O3 O 0.5037(3) 0.2883(3) 0.21855(12) 0.0712(8) Uani 1 1 d . . . . .
O4 O 0.5202(4) 0.1717(2) 0.53428(13) 0.0605(6) Uani 1 1 d . . . . .
N1 N 0.6095(3) 0.3106(2) 0.43193(12) 0.0338(5) 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 C6 1.391(4) . ?
C1 C2 1.391(3) . ?
C1 N1 1.418(3) . ?
C2 C3 1.387(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(4) . ?
C4 C9 1.510(4) . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.456(3) . ?
C7 O1 1.198(3) . ?
C7 C8 1.559(4) . ?
C8 F1 1.375(3) . ?
C8 N1 1.447(3) . ?
C8 C10 1.534(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O3 1.182(3) . ?
C10 O2 1.312(3) . ?
C11 O2 1.447(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O4 1.206(4) . ?
C12 N1 1.386(3) . ?
C12 C13 1.501(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C6 C1 C2 119.5(2) . . ?
C6 C1 N1 110.9(2) . . ?
C2 C1 N1 129.6(2) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 123.9(2) . . ?
C2 C3 H3 118.1 . . ?
C4 C3 H3 118.1 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C9 121.4(3) . . ?
C3 C4 C9 120.6(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 121.8(2) . . ?
C5 C6 C7 129.3(2) . . ?
C1 C6 C7 108.9(2) . . ?
O1 C7 C6 132.0(3) . . ?
O1 C7 C8 122.2(2) . . ?
C6 C7 C8 105.8(2) . . ?
F1 C8 N1 112.5(2) . . ?
F1 C8 C10 108.12(19) . . ?
N1 C8 C10 114.6(2) . . ?
F1 C8 C7 108.3(2) . . ?
N1 C8 C7 103.95(19) . . ?
C10 C8 C7 109.2(2) . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 O2 126.9(3) . . ?
O3 C10 C8 123.6(2) . . ?
O2 C10 C8 109.39(19) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 N1 120.5(3) . . ?
O4 C12 C13 122.0(3) . . ?
N1 C12 C13 117.5(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 O2 C11 117.1(2) . . ?
C12 N1 C1 125.2(2) . . ?
C12 N1 C8 124.9(2) . . ?
C1 N1 C8 109.7(2) . . ?

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
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C9 -179.8(3) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C9 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 -178.2(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 C7 178.8(2) . . . . ?
N1 C1 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 O1 6.9(5) . . . . ?
C1 C6 C7 O1 -171.5(3) . . . . ?
C5 C6 C7 C8 -175.8(3) . . . . ?
C1 C6 C7 C8 5.7(3) . . . . ?
O1 C7 C8 F1 49.4(3) . . . . ?
C6 C7 C8 F1 -128.2(2) . . . . ?
O1 C7 C8 N1 169.2(3) . . . . ?
C6 C7 C8 N1 -8.3(3) . . . . ?
O1 C7 C8 C10 -68.1(3) . . . . ?
C6 C7 C8 C10 114.3(2) . . . . ?
F1 C8 C10 O3 -19.1(4) . . . . ?
N1 C8 C10 O3 -145.4(3) . . . . ?
C7 C8 C10 O3 98.5(3) . . . . ?
F1 C8 C10 O2 164.6(2) . . . . ?
N1 C8 C10 O2 38.3(3) . . . . ?
C7 C8 C10 O2 -77.8(3) . . . . ?
O3 C10 O2 C11 1.7(5) . . . . ?
C8 C10 O2 C11 177.9(2) . . . . ?
O4 C12 N1 C1 -3.4(4) . . . . ?
C13 C12 N1 C1 178.5(2) . . . . ?
O4 C12 N1 C8 -177.8(3) . . . . ?
C13 C12 N1 C8 4.1(4) . . . . ?
C6 C1 N1 C12 179.9(2) . . . . ?
C2 C1 N1 C12 0.4(4) . . . . ?
C6 C1 N1 C8 -5.0(3) . . . . ?
C2 C1 N1 C8 175.5(3) . . . . ?
F1 C8 N1 C12 -59.8(3) . . . . ?
C10 C8 N1 C12 64.2(3) . . . . ?
C7 C8 N1 C12 -176.7(2) . . . . ?
F1 C8 N1 C1 125.0(2) . . . . ?
C10 C8 N1 C1 -111.0(2) . . . . ?
C7 C8 N1 C1 8.1(2) . . . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.057

