# Electronic Supplementary Material (ESI) for Green 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2070059'
loop_
_audit_author_name
_audit_author_address
'Goutam Brahmachari'
;Visva Bharati University 
India
;
_audit_update_record             
;
2021-03-12 deposited with the CCDC.	2021-05-26 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         'C17 H8 F6 N2 O3'
_chemical_formula_sum            'C17 H8 F6 N2 O3'
_chemical_formula_weight         402.25

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'
O O 0.0106 0.0060 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.1491(11)
_cell_length_b                   7.2268(4)
_cell_length_c                   13.9772(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.130(4)
_cell_angle_gamma                90
_cell_volume                     3144.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.01(11)
_cell_measurement_reflns_used    1450
_cell_measurement_theta_min      2.6160
_cell_measurement_theta_max      27.5610

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.164
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.24542
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crys Alis Red'
_exptl_absorpt_special_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150.01(11)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_reflns_number            4195
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.617
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             2733
_reflns_number_gt                1788
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_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     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     285
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1339
_refine_ls_R_factor_gt           0.1088
_refine_ls_wR_factor_ref         0.3394
_refine_ls_wR_factor_gt          0.2891
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_restrained_S_all      1.193
_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
O1 O 0.77450(8) 0.6611(5) 0.2879(2) 0.0409(8) Uani 1 1 d . . . . .
O4 O 0.75899(8) 0.4716(5) 0.5611(2) 0.0454(9) Uani 1 1 d . . . . .
N9 N 0.68945(10) 0.4650(5) 0.4202(3) 0.0346(9) Uani 1 1 d . . . . .
O2 O 0.70717(9) 0.6079(5) 0.2468(2) 0.0526(10) Uani 1 1 d . . . . .
N10 N 0.68038(10) 0.4047(5) 0.5057(3) 0.0364(9) Uani 1 1 d . . . . .
C8A C 0.80832(12) 0.6616(6) 0.3545(3) 0.0332(10) Uani 1 1 d . . . . .
C6 C 0.87974(12) 0.6752(6) 0.4782(3) 0.0352(10) Uani 1 1 d . . . . .
H6 H 0.903729 0.680717 0.519789 0.042 Uiso 1 1 calc R U . . .
C5 C 0.84139(12) 0.6073(5) 0.5094(3) 0.0329(10) Uani 1 1 d . . . . .
H5 H 0.839523 0.566278 0.572179 0.039 Uiso 1 1 calc R U . . .
C3 C 0.72891(11) 0.5251(6) 0.4054(3) 0.0307(9) Uani 1 1 d . . . . .
C4A C 0.80501(12) 0.5997(5) 0.4467(3) 0.0311(9) Uani 1 1 d . . . . .
C11 C 0.63785(11) 0.3461(5) 0.5227(3) 0.0331(10) Uani 1 1 d . . . . .
C7 C 0.88235(12) 0.7359(6) 0.3833(3) 0.0387(11) Uani 1 1 d . . . . .
H7 H 0.908386 0.779443 0.361854 0.046 Uiso 1 1 calc R U . . .
C4 C 0.76399(11) 0.5268(6) 0.4783(3) 0.0349(10) Uani 1 1 d . . . . .
C16 C 0.60625(12) 0.3423(6) 0.4503(3) 0.0334(10) Uani 1 1 d . . . . .
H16 H 0.612358 0.377125 0.388197 0.040 Uiso 1 1 calc R U . . .
C13 C 0.58747(12) 0.2444(6) 0.6357(3) 0.0356(10) Uani 1 1 d . . . . .
C14 C 0.55541(12) 0.2388(5) 0.5642(3) 0.0343(10) Uani 1 1 d . . . . .
H14 H 0.527609 0.204021 0.578300 0.041 Uiso 1 1 calc R U . . .
C15 C 0.56516(12) 0.2852(5) 0.4726(3) 0.0326(10) Uani 1 1 d . . . . .
C12 C 0.62911(12) 0.2978(6) 0.6150(3) 0.0348(10) Uani 1 1 d . . . . .
H12 H 0.650640 0.300676 0.662891 0.042 Uiso 1 1 calc R U . . .
C8 C 0.84702(13) 0.7319(6) 0.3217(3) 0.0391(11) Uani 1 1 d . . . . .
H8 H 0.848742 0.775068 0.259241 0.047 Uiso 1 1 calc R U . . .
C2 C 0.73447(12) 0.5975(6) 0.3098(3) 0.0383(10) Uani 1 1 d . . . . .
C17 C 0.57794(12) 0.2029(6) 0.7363(3) 0.0457(12) Uani 1 1 d D . . . .
C18 C 0.53003(13) 0.2830(7) 0.3953(3) 0.0426(11) Uani 1 1 d . . . . .
F4 F 0.50533(10) 0.1346(6) 0.4024(2) 0.0864(13) Uani 1 1 d . . . . .
F5 F 0.50502(10) 0.4313(6) 0.3983(2) 0.0808(12) Uani 1 1 d . . . . .
F6 F 0.54443(8) 0.2810(4) 0.3080(2) 0.0562(9) Uani 1 1 d . . . . .
F1A F 0.6126(4) 0.140(4) 0.7823(10) 0.106(8) Uani 0.44(3) 1 d D . P A 1
F2A F 0.5371(3) 0.172(4) 0.7565(11) 0.099(7) Uani 0.44(3) 1 d D . P A 1
F3A F 0.5896(7) 0.341(2) 0.7962(12) 0.088(6) Uani 0.44(3) 1 d D . P A 1
F1B F 0.6015(5) 0.0734(16) 0.7810(7) 0.078(4) Uani 0.56(3) 1 d D . P A 2
F2B F 0.5483(5) 0.073(2) 0.7405(8) 0.092(5) Uani 0.56(3) 1 d D . P A 2
F3B F 0.5654(10) 0.347(2) 0.7834(11) 0.133(8) Uani 0.56(3) 1 d D . P A 2
H10 H 0.7009(18) 0.407(8) 0.551(4) 0.063(16) Uiso 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
O1 C2 1.374(5) . ?
O1 C8A 1.379(5) . ?
O4 C4 1.240(5) . ?
N9 N10 1.312(5) . ?
N9 C3 1.327(5) . ?
O2 C2 1.204(5) . ?
N10 C11 1.419(5) . ?
N10 H10 0.88(6) . ?
C8A C4A 1.372(6) . ?
C8A C8 1.401(6) . ?
C6 C5 1.377(5) . ?
C6 C7 1.402(6) . ?
C6 H6 0.9300 . ?
C5 C4A 1.408(5) . ?
C5 H5 0.9300 . ?
C3 C2 1.451(6) . ?
C3 C4 1.466(5) . ?
C4A C4 1.465(5) . ?
C11 C12 1.373(6) . ?
C11 C16 1.386(5) . ?
C7 C8 1.373(6) . ?
C7 H7 0.9300 . ?
C16 C15 1.391(6) . ?
C16 H16 0.9300 . ?
C13 C14 1.388(6) . ?
C13 C12 1.394(6) . ?
C13 C17 1.478(6) . ?
C14 C15 1.368(6) . ?
C14 H14 0.9300 . ?
C15 C18 1.509(6) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C17 F3B 1.298(8) . ?
C17 F1A 1.317(8) . ?
C17 F2B 1.317(7) . ?
C17 F1B 1.331(8) . ?
C17 F2A 1.331(8) . ?
C17 F3A 1.342(9) . ?
C18 F6 1.316(5) . ?
C18 F4 1.326(5) . ?
C18 F5 1.327(6) . ?
F1A F3A 1.63(4) . ?
F1B F2B 1.73(3) . ?

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
C2 O1 C8A 121.8(3) . . ?
N10 N9 C3 118.8(3) . . ?
N9 N10 C11 119.0(4) . . ?
N9 N10 H10 118(4) . . ?
C11 N10 H10 123(4) . . ?
C4A C8A O1 123.4(3) . . ?
C4A C8A C8 121.4(4) . . ?
O1 C8A C8 115.2(4) . . ?
C5 C6 C7 119.5(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C6 C5 C4A 120.3(4) . . ?
C6 C5 H5 119.8 . . ?
C4A C5 H5 119.8 . . ?
N9 C3 C2 113.8(3) . . ?
N9 C3 C4 124.5(4) . . ?
C2 C3 C4 121.7(3) . . ?
C8A C4A C5 119.0(3) . . ?
C8A C4A C4 119.8(4) . . ?
C5 C4A C4 121.2(4) . . ?
C12 C11 C16 121.4(3) . . ?
C12 C11 N10 116.9(4) . . ?
C16 C11 N10 121.7(4) . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
O4 C4 C4A 122.6(3) . . ?
O4 C4 C3 122.0(3) . . ?
C4A C4 C3 115.5(4) . . ?
C11 C16 C15 118.4(4) . . ?
C11 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 C17 121.0(4) . . ?
C12 C13 C17 118.4(4) . . ?
C15 C14 C13 119.2(3) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C14 C15 C16 121.4(4) . . ?
C14 C15 C18 119.2(4) . . ?
C16 C15 C18 119.4(4) . . ?
C11 C12 C13 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C7 C8 C8A 118.8(4) . . ?
C7 C8 H8 120.6 . . ?
C8A C8 H8 120.6 . . ?
O2 C2 O1 116.0(4) . . ?
O2 C2 C3 126.2(4) . . ?
O1 C2 C3 117.8(4) . . ?
F3B C17 F2B 108.7(9) . . ?
F3B C17 F1B 119.8(11) . . ?
F2B C17 F1B 81.7(14) . . ?
F1A C17 F2A 127.6(13) . . ?
F1A C17 F3A 75.8(19) . . ?
F2A C17 F3A 103.4(10) . . ?
F3B C17 C13 113.2(8) . . ?
F1A C17 C13 110.1(7) . . ?
F2B C17 C13 110.6(6) . . ?
F1B C17 C13 117.5(6) . . ?
F2A C17 C13 117.6(7) . . ?
F3A C17 C13 112.6(8) . . ?
F6 C18 F4 106.2(4) . . ?
F6 C18 F5 105.0(4) . . ?
F4 C18 F5 107.9(4) . . ?
F6 C18 C15 113.7(3) . . ?
F4 C18 C15 111.2(4) . . ?
F5 C18 C15 112.4(4) . . ?
C17 F1A F3A 52.8(11) . . ?
C17 F3A F1A 51.4(10) . . ?
C17 F1B F2B 48.8(7) . . ?
C17 F2B F1B 49.5(8) . . ?

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
C3 N9 N10 C11 177.9(3) . . . . ?
C2 O1 C8A C4A 0.0(6) . . . . ?
C2 O1 C8A C8 -179.5(4) . . . . ?
C7 C6 C5 C4A -0.3(6) . . . . ?
N10 N9 C3 C2 -176.8(3) . . . . ?
N10 N9 C3 C4 1.0(6) . . . . ?
O1 C8A C4A C5 -179.5(3) . . . . ?
C8 C8A C4A C5 0.0(6) . . . . ?
O1 C8A C4A C4 0.6(6) . . . . ?
C8 C8A C4A C4 -179.9(4) . . . . ?
C6 C5 C4A C8A -0.3(6) . . . . ?
C6 C5 C4A C4 179.6(4) . . . . ?
N9 N10 C11 C12 -175.1(3) . . . . ?
N9 N10 C11 C16 3.2(6) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
C8A C4A C4 O4 -178.9(4) . . . . ?
C5 C4A C4 O4 1.2(6) . . . . ?
C8A C4A C4 C3 0.5(6) . . . . ?
C5 C4A C4 C3 -179.4(3) . . . . ?
N9 C3 C4 O4 -0.4(6) . . . . ?
C2 C3 C4 O4 177.2(4) . . . . ?
N9 C3 C4 C4A -179.8(4) . . . . ?
C2 C3 C4 C4A -2.2(6) . . . . ?
C12 C11 C16 C15 -1.0(6) . . . . ?
N10 C11 C16 C15 -179.3(4) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C17 C13 C14 C15 177.4(4) . . . . ?
C13 C14 C15 C16 -1.7(6) . . . . ?
C13 C14 C15 C18 -178.7(3) . . . . ?
C11 C16 C15 C14 2.0(6) . . . . ?
C11 C16 C15 C18 179.0(3) . . . . ?
C16 C11 C12 C13 -0.1(6) . . . . ?
N10 C11 C12 C13 178.2(3) . . . . ?
C14 C13 C12 C11 0.4(6) . . . . ?
C17 C13 C12 C11 -176.6(4) . . . . ?
C6 C7 C8 C8A -1.6(6) . . . . ?
C4A C8A C8 C7 1.0(7) . . . . ?
O1 C8A C8 C7 -179.5(4) . . . . ?
C8A O1 C2 O2 178.3(4) . . . . ?
C8A O1 C2 C3 -1.7(6) . . . . ?
N9 C3 C2 O2 0.7(7) . . . . ?
C4 C3 C2 O2 -177.1(4) . . . . ?
N9 C3 C2 O1 -179.3(3) . . . . ?
C4 C3 C2 O1 2.8(6) . . . . ?
C14 C13 C17 F3B -87.3(16) . . . . ?
C12 C13 C17 F3B 89.8(16) . . . . ?
C14 C13 C17 F1A 153.4(14) . . . . ?
C12 C13 C17 F1A -29.5(14) . . . . ?
C14 C13 C17 F2B 35.0(12) . . . . ?
C12 C13 C17 F2B -147.9(11) . . . . ?
C14 C13 C17 F1B 126.3(9) . . . . ?
C12 C13 C17 F1B -56.6(9) . . . . ?
C14 C13 C17 F2A -4.1(16) . . . . ?
C12 C13 C17 F2A 172.9(15) . . . . ?
C14 C13 C17 F3A -124.1(11) . . . . ?
C12 C13 C17 F3A 52.9(12) . . . . ?
C14 C15 C18 F6 -162.9(4) . . . . ?
C16 C15 C18 F6 20.0(5) . . . . ?
C14 C15 C18 F4 -43.1(5) . . . . ?
C16 C15 C18 F4 139.8(4) . . . . ?
C14 C15 C18 F5 78.0(5) . . . . ?
C16 C15 C18 F5 -99.1(5) . . . . ?
F2A C17 F1A F3A -96(2) . . . . ?
C13 C17 F1A F3A 109.2(9) . . . . ?
F2A C17 F3A F1A 125.9(13) . . . . ?
C13 C17 F3A F1A -106.2(11) . . . . ?
F3B C17 F1B F2B 106.9(14) . . . . ?
C13 C17 F1B F2B -109.0(10) . . . . ?
F3B C17 F2B F1B -118.7(10) . . . . ?
C13 C17 F2B F1B 116.4(6) . . . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.129

