# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_SP302F
_audit_block_doi                 10.5517/ccdc.csd.cc2l0vxd
_database_code_depnum_ccdc_archive 'CCDC 2384114'
loop_
_audit_author_name
_audit_author_address
'P Rajalakshmi'
;Christ college of science and management
India
;
_audit_update_record             
;
2024-09-14 deposited with the CCDC.	2024-11-04 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         'C12 H8 F5 N3 O2'
_chemical_formula_sum            'C12 H8 F5 N3 O2'
_chemical_formula_weight         321.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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                   5.2116(2)
_cell_length_b                   7.7885(3)
_cell_length_c                   16.4336(7)
_cell_angle_alpha                97.903(2)
_cell_angle_beta                 98.647(2)
_cell_angle_gamma                97.738(2)
_cell_volume                     644.93(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)

_cell_measurement_reflns_used    9901
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      69.88
_exptl_crystal_description       block
_exptl_crystal_colour            colourless


_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.103
_exptl_absorpt_coefficient_mu    1.458
_shelx_estimated_absorpt_T_min   0.677
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_T_max  0.8404
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_measurement_device_type  
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'



_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20587
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.756
_diffrn_reflns_theta_max         70.211
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2434
_reflns_number_gt                2022
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'



_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)+(0.1292P)²+0.4810P] 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         2434
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0731
_refine_ls_wR_factor_ref         0.2304
_refine_ls_wR_factor_gt          0.2152
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
C1 C 0.3804(6) 0.6886(4) 0.5720(2) 0.0573(8) Uani 1 1 d . . . . .
H1 H 0.217361 0.616857 0.559773 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5076(8) 0.7418(5) 0.6538(2) 0.0640(9) Uani 1 1 d . . . . .
C3 C 0.7462(7) 0.8457(5) 0.6724(2) 0.0626(8) Uani 1 1 d . . . . .
C4 C 0.8703(7) 0.9002(5) 0.6110(2) 0.0694(9) Uani 1 1 d . . . . .
H4 H 1.034481 0.970604 0.624082 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7485(7) 0.8494(5) 0.5295(2) 0.0618(8) Uani 1 1 d . . . . .
H5 H 0.832295 0.885330 0.487152 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5027(6) 0.7454(4) 0.50897(18) 0.0492(7) Uani 1 1 d . . . . .
C7 C 0.3751(5) 0.6975(4) 0.42135(18) 0.0485(7) Uani 1 1 d . . . . .
C8 C 0.3108(5) 0.6795(4) 0.29188(17) 0.0476(7) Uani 1 1 d . . . . .
C9 C 0.3115(5) 0.6907(4) 0.20107(17) 0.0471(7) Uani 1 1 d . . . . .
H10 H 0.157883 0.742495 0.180500 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5541(6) 0.8072(5) 0.1886(2) 0.0600(8) Uani 1 1 d . . . . .
H10A H 0.708081 0.764373 0.212363 0.090 Uiso 1 1 calc R U . . .
H10B H 0.555937 0.924973 0.215511 0.090 Uiso 1 1 calc R U . . .
H10C H 0.552302 0.806264 0.130056 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0498(6) 0.4218(4) 0.11996(18) 0.0521(7) Uani 1 1 d . . . . .
C12 C 0.0553(7) 0.2486(5) 0.0639(2) 0.0646(9) Uani 1 1 d . . . . .
N1 N 0.4877(5) 0.7496(3) 0.35608(14) 0.0492(6) Uani 1 1 d . . . . .
N2 N 0.1447(6) 0.6037(4) 0.39894(17) 0.0662(8) Uani 1 1 d . . . . .
N3 N 0.2855(5) 0.5150(3) 0.15323(15) 0.0496(6) Uani 1 1 d . . . . .
O1 O 0.0983(4) 0.5895(3) 0.31138(13) 0.0663(7) Uani 1 1 d . . . . .
O2 O -0.1597(4) 0.4646(3) 0.12877(16) 0.0694(7) Uani 1 1 d . . . . .
F1 F 0.8614(5) 0.8942(4) 0.75312(12) 0.0893(8) Uani 1 1 d . . . . .
F2 F 0.3964(6) 0.6940(4) 0.71635(15) 0.1006(9) Uani 1 1 d . . . . .
F3 F -0.0175(9) 0.2606(4) -0.01343(15) 0.1349(14) Uani 1 1 d . . . . .
F4 F -0.1121(6) 0.1200(3) 0.08058(19) 0.1066(9) Uani 1 1 d . . . . .
F5 F 0.2815(6) 0.1930(4) 0.0742(2) 0.1202(12) Uani 1 1 d . . . . .
H3A H 0.415(8) 0.475(5) 0.143(2) 0.066(11) 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
C1 C2 1.387(5) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 F2 1.325(4) . ?
C2 C3 1.357(5) . ?
C3 F1 1.351(4) . ?
C3 C4 1.362(5) . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(4) . ?
C7 N2 1.292(4) . ?
C7 N1 1.380(4) . ?
C8 N1 1.294(4) . ?
C8 O1 1.334(3) . ?
C8 C9 1.507(4) . ?
C9 N3 1.460(4) . ?
C9 C10 1.511(4) . ?
C9 H10 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.207(4) . ?
C11 N3 1.335(4) . ?
C11 C12 1.532(5) . ?
C12 F3 1.290(4) . ?
C12 F5 1.305(4) . ?
C12 F4 1.324(4) . ?
N2 O1 1.409(3) . ?
N3 H3A 0.81(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
C2 C1 C6 118.3(3) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
F2 C2 C3 118.1(3) . . ?
F2 C2 C1 120.6(4) . . ?
C3 C2 C1 121.3(3) . . ?
F1 C3 C2 119.0(3) . . ?
F1 C3 C4 120.0(3) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 120.9(3) . . ?
C5 C6 C7 119.8(3) . . ?
N2 C7 N1 114.2(3) . . ?
N2 C7 C6 122.4(3) . . ?
N1 C7 C6 123.4(3) . . ?
N1 C8 O1 113.5(3) . . ?
N1 C8 C9 129.1(3) . . ?
O1 C8 C9 117.4(2) . . ?
N3 C9 C8 110.0(2) . . ?
N3 C9 C10 111.2(2) . . ?
C8 C9 C10 111.8(2) . . ?
N3 C9 H10 107.9 . . ?
C8 C9 H10 107.9 . . ?
C10 C9 H10 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N3 125.9(3) . . ?
O2 C11 C12 119.1(3) . . ?
N3 C11 C12 115.1(3) . . ?
F3 C12 F5 110.3(4) . . ?
F3 C12 F4 106.4(3) . . ?
F5 C12 F4 104.3(3) . . ?
F3 C12 C11 110.6(3) . . ?
F5 C12 C11 114.1(3) . . ?
F4 C12 C11 110.8(3) . . ?
C8 N1 C7 102.4(2) . . ?
C7 N2 O1 103.9(2) . . ?
C11 N3 C9 121.3(2) . . ?
C11 N3 H3A 118(3) . . ?
C9 N3 H3A 120(3) . . ?
C8 O1 N2 105.9(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 F2 178.6(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
F2 C2 C3 F1 0.8(5) . . . . ?
C1 C2 C3 F1 179.8(3) . . . . ?
F2 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
F1 C3 C4 C5 -179.8(3) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C1 C6 C7 N2 0.9(5) . . . . ?
C5 C6 C7 N2 -178.8(3) . . . . ?
C1 C6 C7 N1 -179.8(3) . . . . ?
C5 C6 C7 N1 0.5(4) . . . . ?
N1 C8 C9 N3 121.8(3) . . . . ?
O1 C8 C9 N3 -60.2(3) . . . . ?
N1 C8 C9 C10 -2.3(4) . . . . ?
O1 C8 C9 C10 175.8(3) . . . . ?
O2 C11 C12 F3 71.0(4) . . . . ?
N3 C11 C12 F3 -107.1(4) . . . . ?
O2 C11 C12 F5 -163.9(3) . . . . ?
N3 C11 C12 F5 17.9(4) . . . . ?
O2 C11 C12 F4 -46.6(4) . . . . ?
N3 C11 C12 F4 135.2(3) . . . . ?
O1 C8 N1 C7 0.3(3) . . . . ?
C9 C8 N1 C7 178.5(3) . . . . ?
N2 C7 N1 C8 -0.6(3) . . . . ?
C6 C7 N1 C8 -179.9(3) . . . . ?
N1 C7 N2 O1 0.6(4) . . . . ?
C6 C7 N2 O1 180.0(3) . . . . ?
O2 C11 N3 C9 -4.3(5) . . . . ?
C12 C11 N3 C9 173.7(3) . . . . ?
C8 C9 N3 C11 89.6(3) . . . . ?
C10 C9 N3 C11 -146.0(3) . . . . ?
N1 C8 O1 N2 0.0(4) . . . . ?
C9 C8 O1 N2 -178.3(3) . . . . ?
C7 N2 O1 C8 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N2 0.93 2.61 3.452(4) 151.0 2_566 yes
N3 H3A O2 0.81(4) 2.28(4) 3.048(3) 160(4) 1_655 yes

_refine_diff_density_max         0.895
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.067

